Citation:  Wen-Bo Mu, Yue Zou, Quan-Rui Wang, Andreas Goeke. A novel synthetic route to rac-(Z)-recifeiolide from cyclooctanone and acetaldehyde[J]. Chinese Chemical Letters, 2015, 26(11): 1393-1396. doi: 10.1016/j.cclet.2015.07.006 shu

    通讯作者: Quan-Rui Wang,
    Andreas Goeke,

English

  • 
    1. [1] M. Kerschbaum, Ü ber Lactone mit großen Ringen-die Träger des vegetabilischen Moschus-Duftes, Chem. Ber. 60 (1927) 902-909.[1] M. Kerschbaum, Ü ber Lactone mit großen Ringen-die Träger des vegetabilischen Moschus-Duftes, Chem. Ber. 60 (1927) 902-909.

    2. [2] (a) I. Shiina, Total synthesis of natural 8- and 9-membered lactones: recent advancements in medium-sized ring formation, Chem. Rev. 107 (2007) 239-273; (b) G. Rousseau, Medium ring lactones, Tetrahedron 51 (1995) 2777-2849; (c) D. Poth, P.S. Peram, M. Vences, S. Schulz, Macrolides and alcohols as scent gland constituents of the Madagascan frog mantidactylus femoralis and their intraspecific diversity, J. Nat. Prod. 76 (2013) 1548-1558; (d) A. Parenty, X. Moreau, J.M. Campagne, Macrolactonizations in the total synthesis of natural products, Chem. Rev. 106 (2006) 911-939; (e) A. Parenty, X. Moreau, J.M. Gilles Niel, Campagne, Update 1 of: macrolactonizations in the total synthesis of natural products, Chem. Rev. 113 (2013), PR1- PR40; (f) Z.X. Chen, D.L. Liu, W.Y. Gao, T.J. Zhang, A new macrolide and glycosides from the stem of Sargentodoxa cuneate, Chin. Chem. Lett. 20 (2009) 1339-1341.[2] (a) I. Shiina, Total synthesis of natural 8- and 9-membered lactones: recent advancements in medium-sized ring formation, Chem. Rev. 107 (2007) 239-273; (b) G. Rousseau, Medium ring lactones, Tetrahedron 51 (1995) 2777-2849; (c) D. Poth, P.S. Peram, M. Vences, S. Schulz, Macrolides and alcohols as scent gland constituents of the Madagascan frog mantidactylus femoralis and their intraspecific diversity, J. Nat. Prod. 76 (2013) 1548-1558; (d) A. Parenty, X. Moreau, J.M. Campagne, Macrolactonizations in the total synthesis of natural products, Chem. Rev. 106 (2006) 911-939; (e) A. Parenty, X. Moreau, J.M. Gilles Niel, Campagne, Update 1 of: macrolactonizations in the total synthesis of natural products, Chem. Rev. 113 (2013), PR1- PR40; (f) Z.X. Chen, D.L. Liu, W.Y. Gao, T.J. Zhang, A new macrolide and glycosides from the stem of Sargentodoxa cuneate, Chin. Chem. Lett. 20 (2009) 1339-1341.

    3. [3] (a) W. Zhao, Z. Li, J. Sun, A new strategy for efficient synthesis of medium and large ring lactones without high dilution or slow addition, J. Am. Chem. Soc. 135 (2013) 4680-4683; (b) G. Illuminati, L. Mandolini, Ring closure reactions of bifunctional chain molecules, Acc. Chem. Res. 14 (1981) 95-102; (c) A. Gradillas, J. Pé rez-Castells, Macrocyclization by ring-closing metathesis in the total synthesis of natural products: reaction conditions and limitations, Angew. Chem. Int. Ed. 45 (2006) 6086-6101; (d) A. Deiters, S.F. Martin, Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis, Chem. Rev. 104 (2004) 2199-2238; (e) C.J. Hou, X.M. Liang, J.P. Wu, D.Q. Wang, Synthesis of macrocyclic lactones with methoxysulfonyl side chain, Chin. Chem. Lett. 19 (2008) 403-405.[3] (a) W. Zhao, Z. Li, J. Sun, A new strategy for efficient synthesis of medium and large ring lactones without high dilution or slow addition, J. Am. Chem. Soc. 135 (2013) 4680-4683; (b) G. Illuminati, L. Mandolini, Ring closure reactions of bifunctional chain molecules, Acc. Chem. Res. 14 (1981) 95-102; (c) A. Gradillas, J. Pé rez-Castells, Macrocyclization by ring-closing metathesis in the total synthesis of natural products: reaction conditions and limitations, Angew. Chem. Int. Ed. 45 (2006) 6086-6101; (d) A. Deiters, S.F. Martin, Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis, Chem. Rev. 104 (2004) 2199-2238; (e) C.J. Hou, X.M. Liang, J.P. Wu, D.Q. Wang, Synthesis of macrocyclic lactones with methoxysulfonyl side chain, Chin. Chem. Lett. 19 (2008) 403-405.

    4. [4] D.M. Zubrytski, D.G. Kananovich, O.G. Kulinkovich, A highly stereoselective route to medium-ring-sized trans-alkenolides via oxidative fragmentation of bicyclic oxycyclopropane precursors: application to the synthesis of (+)-recifeiolide, Tetrahedron 70 (2014) 2944-2950.[4] D.M. Zubrytski, D.G. Kananovich, O.G. Kulinkovich, A highly stereoselective route to medium-ring-sized trans-alkenolides via oxidative fragmentation of bicyclic oxycyclopropane precursors: application to the synthesis of (+)-recifeiolide, Tetrahedron 70 (2014) 2944-2950.

    5. [5] (a) Y. Zou, H. Mouhib, W. Stahl, et al., Efficient macrocyclization by a novel oxyoxonia- Cope reaction: synthesis and olfactory properties of new macrocyclic musks, Chem. Eur. J. 18 (2012) 7010-7015; (b) Y. Zou, C. Ding, L. Zhou, et al., Tandem cross-dimerisation/oxonia-Cope reaction of carbonyl compounds to homoallylic esters and lactones, Angew. Chem. Int. Ed. 51 (2012) 5647-5651; (c) L. Zhou, Z. Li, Y. Zou, et al., Tandem nucleophilic addition/oxy-2-azonia-Cope rearrangement for the formation of homoallylic amides and lactams: total synthesis and structural verification of motuporamine G, J. Am. Chem. Soc. 134 (2012) 20009-20012; (d) W. Mu, L. Zhou, Y. Zou, Q. Wang, A. Goeke, Irreversible oxy-2-azonia-Cope rearrangements for the synthesis of functionalized allyl a-amino acid derivatives, Eur. J. Org. Chem. (2014) 2379-2385; (e) Y. Zou, L. Zhou, C. Ding, et al., Novel oxy-oxonia(azonia)-Cope reaction: serendipitous discovery and its application to the synthesis of macrocyclic musks, Chem. Biodivers. 11 (2014) 1608-1628.[5] (a) Y. Zou, H. Mouhib, W. Stahl, et al., Efficient macrocyclization by a novel oxyoxonia- Cope reaction: synthesis and olfactory properties of new macrocyclic musks, Chem. Eur. J. 18 (2012) 7010-7015; (b) Y. Zou, C. Ding, L. Zhou, et al., Tandem cross-dimerisation/oxonia-Cope reaction of carbonyl compounds to homoallylic esters and lactones, Angew. Chem. Int. Ed. 51 (2012) 5647-5651; (c) L. Zhou, Z. Li, Y. Zou, et al., Tandem nucleophilic addition/oxy-2-azonia-Cope rearrangement for the formation of homoallylic amides and lactams: total synthesis and structural verification of motuporamine G, J. Am. Chem. Soc. 134 (2012) 20009-20012; (d) W. Mu, L. Zhou, Y. Zou, Q. Wang, A. Goeke, Irreversible oxy-2-azonia-Cope rearrangements for the synthesis of functionalized allyl a-amino acid derivatives, Eur. J. Org. Chem. (2014) 2379-2385; (e) Y. Zou, L. Zhou, C. Ding, et al., Novel oxy-oxonia(azonia)-Cope reaction: serendipitous discovery and its application to the synthesis of macrocyclic musks, Chem. Biodivers. 11 (2014) 1608-1628.

    6. [6] For isolation and an early synthesis, see: (a) RF. Vesonder, F.H. Stodola, L.J. Wickerham, J.J. Ellis, W.K. Rohwedder, 11- Hydroxy-trans-8-dodecenoic acid lactone, a 12-membered-ring compound from a fungus, Can. J. Chem. 49 (1971) 2029-2032; (b) E.J. Corey, P. Ulrich, J.M. Fitzpatrick, A stereoselective synthesis of (±)-11- hydroxy-trans-8-dodecenoic acid lactone, a naturally occurring macrolide from Cephalosporium recifei, J. Am. Chem. Soc. 98 (1976) 222-224.[6] For isolation and an early synthesis, see: (a) RF. Vesonder, F.H. Stodola, L.J. Wickerham, J.J. Ellis, W.K. Rohwedder, 11- Hydroxy-trans-8-dodecenoic acid lactone, a 12-membered-ring compound from a fungus, Can. J. Chem. 49 (1971) 2029-2032; (b) E.J. Corey, P. Ulrich, J.M. Fitzpatrick, A stereoselective synthesis of (±)-11- hydroxy-trans-8-dodecenoic acid lactone, a naturally occurring macrolide from Cephalosporium recifei, J. Am. Chem. Soc. 98 (1976) 222-224.

    7. [7] X. Huang, C. Craita, L. Awad, P. Vogel, Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids, Chem. Commun. 10 (2005) 1297-1299.[7] X. Huang, C. Craita, L. Awad, P. Vogel, Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids, Chem. Commun. 10 (2005) 1297-1299.

    8. [8] H.H. Wasserman, R.J. Gambale, M.J. Pulwer, Activated carboxylates from the photooxygenation of oxazoles: application to the synthesis of recifeiolide, curvularin and macrolides, Tetrahedron 37 (1981) 4059-4067.[8] H.H. Wasserman, R.J. Gambale, M.J. Pulwer, Activated carboxylates from the photooxygenation of oxazoles: application to the synthesis of recifeiolide, curvularin and macrolides, Tetrahedron 37 (1981) 4059-4067.

    9. [9] J.R. Mahajan, I.S. Resck, Synthesis of (±)-recifeiolide and its homologs via acetylenic lactones, Synth. Commun. 26 (1996) 3809-3819.[9] J.R. Mahajan, I.S. Resck, Synthesis of (±)-recifeiolide and its homologs via acetylenic lactones, Synth. Commun. 26 (1996) 3809-3819.

    10. [10] A. Fuerstner, K. Langemann, Macrocycles by ring-closing metathesis, Synthesis (1997) 792-803.[10] A. Fuerstner, K. Langemann, Macrocycles by ring-closing metathesis, Synthesis (1997) 792-803.

    11. [11] K. Okuma, S. Hirabayashi, M. Ono, K. Shioji, H. Matsuyama, H.J. Bestmann, An efficient synthesis of (R)-(+)-recifeiolide and related macrolides by using enantiomerically pure (R)-(-)-5-methyl-2,2,2-triphenyl-1,2λ5-oxaphospholane, Tetrahedron 54 (1998) 4243-4250.[11] K. Okuma, S. Hirabayashi, M. Ono, K. Shioji, H. Matsuyama, H.J. Bestmann, An efficient synthesis of (R)-(+)-recifeiolide and related macrolides by using enantiomerically pure (R)-(-)-5-methyl-2,2,2-triphenyl-1,2λ5-oxaphospholane, Tetrahedron 54 (1998) 4243-4250.

    12. [12] I. Fleming, A. Barbero, D. Walter, Stereochemical control in organic synthesis using silicon-containing compounds, Chem. Rev. 97 (1997) 2063-2192.[12] I. Fleming, A. Barbero, D. Walter, Stereochemical control in organic synthesis using silicon-containing compounds, Chem. Rev. 97 (1997) 2063-2192.

    13. [13] L.E. Overman, A. Castaneda, T.A. Blumenkopf, Acetal-initiated cyclizations of vinylsilanes. A general synthesis of allylically unsaturated oxacyclic, J. Am. Chem. Soc. 108 (1986) 1303-1304.[13] L.E. Overman, A. Castaneda, T.A. Blumenkopf, Acetal-initiated cyclizations of vinylsilanes. A general synthesis of allylically unsaturated oxacyclic, J. Am. Chem. Soc. 108 (1986) 1303-1304.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1698
  • HTML全文浏览量:  43
文章相关
  • 发布日期:  2015-07-08
  • 收稿日期:  2015-04-15
  • 网络出版日期:  2015-06-16
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章