An efficient derivation of the versatile chiron antipode 1-tert-butyldimethylsilylpenta-1,4-diyn-3-ol:: Application to the synthesis of (15E,R,R)-duryne

被引：37

作者：

Sharma, A ^{[1
]}

Chattopadhyay, S ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Bioorgan Div, Bombay 400085, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 18期

关键词：

D O I：

10.1021/jo9800513

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title chiron, 1-tert-butyldimethylsilylpenta-1,4-diyn-3-ol (5), an essential segment of various bioactive polyacetylenic alcohols, has been efficiently resolved via a lipase-catalyzed acylation strategy. Lipases from different Pseudomonas species and Candida rugosa (CRL) furnished its (S)-antipode (as esters) with 86-96% ee. However, the (R)-alcohol 5 could be prepared with acceptable enantiomeric purity (93% ee) only using CRL-vinyl acetate-diisopropyl ether as the reagent protocol and under double filtration conditions. The chiron alcohol was then extended to the target compound (15E,R,R)-duryne (I) by its pyranylation, alkylation with the required achiral C-20-alpha,omega-dibromide 15, and suitable functionalization.

引用

页码：6128 / 6131

页数：4

共 17 条

[1]

Campbell K.N., 1941, J. Am. Chem. Soc., V63, P216, DOI DOI 10.1021/JA01846A050

[2]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[3] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[4] SYNTHESIS OF (+/-)DURYNE [J].

DESHPANDE, VH ;

UPADHYE, BK ;

WAKHARKAR, RD .

TETRAHEDRON LETTERS, 1989, 30 (15) :1991-1992

[5] BIOACTIVE MARINE METABOLITES .20. PETROSYNOL AND PETROSYNONE, ANTIMICROBIAL C30 POLYACETYLENES FROM THE MARINE SPONGE PETROSIA SP - DETERMINATION OF THE ABSOLUTE-CONFIGURATION [J].

FUSETANI, N ;

SHIRAGAKI, T ;

MATSUNAGA, S ;

HASHIMOTO, K .

TETRAHEDRON LETTERS, 1987, 28 (37) :4313-4314

[6] ENANTIOSELECTIVE HYDROLYSES BY BAKERS-YEAST .3. MICROBIAL RESOLUTION OF ALKYNYL ESTERS USING LYOPHILIZED YEAST [J].

GLANZER, BI ;

FABER, K ;

GRIENGL, H .

TETRAHEDRON, 1987, 43 (24) :5791-5796

[7] NEW ACETYLENIC ALCOHOLS FROM THE SPONGE CRIBROCHALINA-VASCULUM [J].

GUNASEKERA, SP ;

FAIRCLOTH, GT .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6223-6225

[8] FURTHER STRUCTURAL STUDIES ON THE PETROFORMYNES [J].

GUO, YW ;

GAVAGNIN, M ;

TRIVELLONE, E ;

CIMINO, G .

JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (05) :712-722

[9] Antitumor activity and stereochemistry of acetylenic alcohols from the sponge Cribrochalina vasculum [J].

Hallock, YF ;

Cardellina, JH ;

Blaschak, MS ;

Alexander, MR ;

Prather, TR ;

Shoemaker, RH ;

Boyd, MR .

JOURNAL OF NATURAL PRODUCTS, 1995, 58 (12) :1801-1807

[10]

KANG K, 1985, SYNTHESIS-STUTTGART, P1161

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