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Citation: ZHANG Da-Hai, LI Xian-Guo, SON Byeng-Hwa. Stereo-chemistry of Natural Product Botrytinone[J]. Chinese Journal of Applied Chemistry, ;2008, 25(12): 1425-1429. shu

Stereo-chemistry of Natural Product Botrytinone

1.
aCollege of Chemistry & Chemical Engineering, Ocean University of China, Qingdao 266003;
2.
b Department of Chemistry, Pukyong National University, Busan 608-737, Korea

Corresponding author: ZHANG Da-Hai,
Received Date: 25 November 2007
Available Online: 28 March 2008
Fund Project: 韩国科学与工程基金(KOSEF):R01-2004-000-10467-0支持 (KOSEF)

In the molecule of the natural product botrytinone isolated from the metabolites of marine-derived fungus Botrytis sp.,there are three chiral centers.2D NOE spectrum and quantum chemistry calculation all confirmed that the 7-CH₃ and 5-OH are on the same side and the 4-OH on the other side.On the basis of X-ray diffraction analysis,its p-bromobenzoyl derivative C₂₁H₁₅Br₂ClO₅ belongs to triclinic system with space group P-1,a=0.668 47(5) nm,b=1.218 90(9) nm,c=1.307 8(1) nm,α=83.984(1)°,β=80.366(1)°,γ=84.514(1)°,V=1.041 5(1) nm³,and Z=2,which further support its relative structure.The CD spectrum of its p-bromobenzoyl derivative shows minor Cotton effection at 243 nm(Δε-39.9).The absolute configuration was elucidated by CD exciton chirality method.Finally it was determined to be(4R,5S,6R)-4,5-dihydroxy-3-(1-hydroxyethyl)-2-cyclopenten-1-one.
- botrytinone,
- 2D NOE spectrum,
- X-ray diffraction,
- CD exciton chirality method
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