New entry to the synthesis of clerodane diterpenes. The first enantioselective syntheses of 7-oxo-kolavenic acid and methyl solidagonate

被引：8

作者：

Kato, M ^{[1
]}

Kosugi, H

Ichiyanagi, T

Hagiwara, H

Kodaira, A

Kusakari, T

Suzuki, T

Ando, M

Lee, J

Drechsel, P

Vogler, B

机构：

[1] Tohoku Univ, Inst Chem React Sci, Aoba Ku, Sendai, Miyagi 9808577, Japan

[2] Niigata Univ, Grad Sch Sci & Technol, Ikarashi 9502181, Japan

[3] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

来源：

TETRAHEDRON | 2001年 / 57卷 / 39期

关键词：

natural products; asymmetric synthesis; cleavage reactions; ene reactions;

D O I：

10.1016/S0040-4020(01)00821-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using (1S,5S)-(-)-verbenone (8b), readily obtainable from (+)-nopinone (3), as the chiral source, we have established the general method for preparation of three kinds of key intermediates, conjugate enones 9 and 10 for the syntheses of neo-trans-clerodanes and ae C11 for those of neo-cis-clerodanes. Starting with the compound 10, the first enantioselective syntheses of (-)-(5R,8S,9S,10R)-7-oxo-cleroda-3,13E-dien-15-oic cid (7-oxo-kolavenic acid) (1) and solidagonic acid (2) as its methyl ester (48) were achieved. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8243 / 8256

页数：14

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