Concise total synthesis of (+/-)-palominol and (+/-)-dolabellatrienone via a dianion-accelerated oxy-Cope rearrangement

被引：27

作者：

Corey, EJ ^{[1
]}

Kania, RS ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 08期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)10614-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of (+/-)-palominol (1) and (+/-)-dolabellatrienone (2) starting from farnesol is reported. Noteworthy steps include an intramolecular pinacol coupling to form a 15-membered carbocyclic diol and subsequent dianion-accelerated oxy-Cope rearrangement to form the 11,5-trans-fused ring system of the dolabellanes. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：741 / 744

页数：4

共 32 条

[1]

CACERES J, 1990, TETRAHEDRON, V46, P3422

[2] ENANTIOSELECTIVE TOTAL SYNTHESIS OF BETA-ELEMENE AND FUSCOL BASED ON ENANTIOCONTROLLED IRELAND-CLAISEN REARRANGEMENT [J].

COREY, EJ ;

ROBERTS, BE ;

DIXON, BR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :193-196

[3] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS [J].

COREY, EJ ;

LEE, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4026-4028

[4] First enantioselective total synthesis of a naturally occurring dolabellane. Revision of absolute configuration [J].

Corey, EJ ;

Kania, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) :1229-1230

[5]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[6]

COREY EJ, 1978, TETRAHEDRON LETT, V12, P1051

[7] DIRECT OXIDATION OF TERTIARY ALLYLIC ALCOHOLS - SIMPLE AND EFFECTIVE METHOD FOR ALKYLATIVE CARBONYL TRANSPOSITION [J].

DAUBEN, WG ;

MICHNO, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :682-685

[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[9] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[10] MARINE NATURAL-PRODUCTS FROM ATLANTIC ZONE .35. A NEW DITERPENE FROM APLYSIA-DACTYLOMELA [J].

GONZALEZ, AG ;

MARTIN, JD ;

NORTE, M ;

PEREZ, R ;

WEYLER, V ;

RAFII, S ;

CLARDY, J .

TETRAHEDRON LETTERS, 1983, 24 (10) :1075-1076

← 1 2 3 4 →