Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (-)-(6S,2′S)-epi cryptocaryalactone

被引：31

作者：

Sabitha, Gowravaram ^{[1
]}

Bhaskar, V. ^{[1
]}

Reddy, S. Siva Sankara ^{[1
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2008年 / 64卷 / 44期

关键词：

alpha; beta-Unsaturated delta-lactone; Base catalyzed conjugate addition; Z-Wittig olefination; Stereoselective reduction; cis Wittig olefination; 1,3-Polyol;

D O I：

10.1016/j.tet.2008.08.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+)-(6R,2'S)-cryptocaryalactone and (-)-(6S,2'S)-epi cryptocaryalactone is reported based on stereoselective reduction of delta-hydroxy beta-keto ester to install 1,3-polyol system, cis Wittig olefination, and lactonization as the key steps. The synthesis of (-)-(6S,2'S)-epi cryptocaryalactone is also reported using syn-benzylidene acetal formation and a preferential Z-Wittig olefination reaction and lactonization as the key steps. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10207 / 10213

页数：7

共 36 条

[11] THE DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING ME4NHB(OAC)3 [J].

EVANS, DA ;

CHAPMAN, KT .

TETRAHEDRON LETTERS, 1986, 27 (49) :5939-5942

[12] REDUCTION OF BETA-HYDROXY KETONES WITH CATECHOLBORANE - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF SYN 1,3-DIOLS [J].

EVANS, DA ;

HOVEYDA, AH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5190-5192

[13] 2 NEW STYRYL LACTONES, 9-DEOXYGONIOPYPYRONE AND 7-EPI-GONIOFUFURONE, FROM GONIOTHALAMUS-GIGANTEUS [J].

FANG, XP ;

ANDERSON, JE ;

CHANG, CJ ;

MCLAUGHLIN, JL ;

FANWICK, PE .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (04) :1034-1043

[14]

GOVINDACHARI TR, 1972, INDIAN J CHEM, V10, P149

[15]

Hawariah A, 1998, ANTICANCER RES, V18, P4383

[16]

HAWARIAH LPA, 1994, ASIA PAC J PHARMACOL, V9, P273

[17] A 6-substituted-5,6-dihydro-2-pyrone from Cryptocarya strictifolia [J].

Juliawaty, LD ;

Kitajima, M ;

Takayama, H ;

Achmad, SA ;

Aimi, N .

PHYTOCHEMISTRY, 2000, 54 (08) :989-993

[18] SYNTHESES AND ABSOLUTE-CONFIGURATIONS OF (+)-(6R,2'S)-CRYPTOCARYALACTONE AND (-)-(6S,2'S)-EPICRYPTOCARYALACTONE [J].

MEYER, HH .

LIEBIGS ANNALEN DER CHEMIE, 1984, (05) :977-981

[19]

MORI Y, 1994, CHEM PHARM BULL, V42, P2161

[20]

Pihie AHL, 1998, ANTICANCER RES, V18, P1739

← 1 2 3 4 →