Stereocontrolled synthesis of the key intermediate for the enantioselective synthesis of clerodane natural products

被引：4

作者：

Kato, M ^{[1
]}

Kosugi, H ^{[1
]}

Kodaira, A ^{[1
]}

Hagiwara, H ^{[1
]}

Vogler, B ^{[1
]}

机构：

[1] UNIV HOHENHEIM,INST CHEM,D-70599 STUTTGART,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(97)01614-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereocontrolled synthesis of (+)-trans-decalone 7 (R = CH=CH2) from (-)-verbenone (5), readily obtainable from (+)-nopinone (2), is described. The compound 7 possesses four correctly arranged chiral centers, C(5)-C(10)-C(9)-C(8), necessary for the enantioselective synthesis of neo-trans-clerodanes. (C) 1997 Elsevier Science Ltd.

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页码：6845 / 6848

页数：4

相关论文

共 12 条

[1]

Caine D., 1991, Comprehensive Organic Synthesis, V3, P1

[2] THE USE OF 4,4-DISUBSTITUTED NOPINONES FOR NATURAL-PRODUCT SYNTHESIS - SYNTHESIS OF ELEMANOID SESQUITERPENES [J].

KATO, M ;

WATANABE, M ;

VOGLER, B ;

AWEN, BZ ;

MASUDA, Y ;

TOOYAMA, Y ;

YOSHIKOSHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7071-7076

[3] ELECTROPHILE-INITIATED CYCLOBUTANE RING CLEAVAGE OF (+)-CIS-3-METHYLNOPINONE [J].

KATO, M ;

KAMAT, VP ;

TOOYAMA, Y ;

YOSHIKOSHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1536-1538

[4] PREPARATION OF KEY INTERMEDIATES FOR THE ASYMMETRIC-SYNTHESIS OF OXYGENATED ELEMANOIDS [J].

KATO, M ;

KIDO, F ;

WATANABE, M ;

MASUDA, Y ;

AWEN, BZ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (22) :2831-2836

[5] A STEREOCONTROLLED SYNTHESIS OF (4AS,8AR)-(+)-7,7-ETHYLENEDIOXY-4,4,8A-TRIMETHYLOCTAHYDRO-2(1H)-NAPHTHALENONE [J].

KATO, M ;

WATANABE, M ;

MASUDA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (08) :2071-2075

[6] EFFICIENT PREPARATION OF A KEY INTERMEDIATE SUITABLE FOR THE ASYMMETRIC-SYNTHESIS OF (+)-VERNOLEPIN AND (-)-VERNOMENIN [J].

KATO, M ;

KIDO, F ;

MASUDA, Y ;

WATANABE, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (09) :697-698

[7] CLERODANE DITERPENOIDS [J].

MERRITT, AT ;

LEY, SV .

NATURAL PRODUCT REPORTS, 1992, 9 (03) :243-287

[8] CRYSTAL-STRUCTURE OF 3-EPICARYOPTIN AND THE REVERSAL OF THE CURRENTLY ACCEPTED ABSOLUTE-CONFIGURATION OF CLERODIN [J].

ROGERS, D ;

UNAL, GG ;

WILLIAMS, DJ ;

LEY, SV ;

SIM, GA ;

JOSHI, BS ;

RAVINDRANATH, KR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (03) :97-99

[9]

Snider B. B., COMPREHENSIVE ORGANI, V2, P527, DOI DOI 10.1016/B978-0-08-052349-1.00040-8

[10]

THOMAS AF, 1988, SYNTHESIS MONOTERPEN, V7, P275