Expedient synthetic transformation of ptychantins into forskolin

被引：12

作者：

Hagiwara, Hisahiro ^{[1
]}

Tsukagoshi, Masashi ^{[1
]}

Hoshi, Takashi ^{[2
]}

Suzuki, Toshio ^{[2
]}

Hashimoto, Toshihiro ^{[3
]}

Asakawa, Yoshinori ^{[3
]}

机构：

[1] Niigata Univ, Grad Sch Sci & Technol, Nishi Ku, Niigata 9502181, Japan

[2] Niigata Univ, Fac Engn, Nishi Ku, Niigata 9502181, Japan

[3] Tokushima Bunri Univ, Fac Pharmaceut Sci, Yamashiro, Tokushima 7708514, Japan

来源：

SYNLETT | 2008年 / 06期

关键词：

terpenoids; total synthesis; forskolin; labdane diterpenoid;

D O I：

10.1055/s-2008-1042930

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort Ptychanthus striatus in good yield. The I a-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9 alpha-hydroxy group was introduced stereoselectively by epoxidation of Delta(9,11)-enol ether.

引用

页码：929 / 931

页数：3

共 6 条

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Ye, Heping
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ORGANIC LETTERS, 2009, 11 (23) : 5442 - 5444
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[4] INTRAMOLECULAR COUPLING REACTION PROMOTED BY SMI2 IN A SYNTHETIC APPROACH OF FORSKOLIN
ANIES, C
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PRANGE, T
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[5] Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3
Couladouros, EA
Moutsos, VI
Pitsinos, EN
TETRAHEDRON LETTERS, 2004, 45 (41) : 7779 - 7781
[6] Synthesis of novel 1,4-disubstituted-1,2,3-triazole semi synthetic analogues of forskolin by click reaction
Reddy, M. Koteswara
Kumar, K. Santosh
Sreenivas, P.
Krupadanam, G. L. David
Reddy, K. Janardhan
TETRAHEDRON LETTERS, 2011, 52 (49) : 6537 - 6540

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