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
收藏
页码：929 / 931
页数：3
相关论文
共 50 条
  • [1] Synthetic transformation of ptychantin into forskolin and 1,9-dideoxyforskolin
    Hagiwara, Hisahiro
    Takeuchi, Fumihide
    Kudou, Masaru
    Hoshi, Takashi
    Suzuki, Toshio
    Hashimoto, Toshihiro
    Asakawa, Yoshinori
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12): : 4619 - 4624
  • [2] A SYNTHETIC ROUTE TO FORSKOLIN
    NICOLAOU, KC
    KUBOTA, S
    LI, WS
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) : 512 - 514
  • [3] SYNTHETIC ROUTES TO FORSKOLIN
    COLOMBO, MI
    ZINCZUK, J
    RUVEDA, EA
    TETRAHEDRON, 1992, 48 (06) : 963 - 1037
  • [4] A SYNTHETIC ROUTE TO FORSKOLIN
    ZIEGLER, FE
    JAYNES, BH
    SAINDANE, MT
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) : 8115 - 8116
  • [5] SYNTHETIC STUDIES TOWARDS FORSKOLIN
    BHAKUNI, DS
    PURE AND APPLIED CHEMISTRY, 1990, 62 (07) : 1389 - 1392
  • [6] SYNTHETIC STUDIES TOWARDS FORSKOLIN
    BARALDI, PG
    BARCO, A
    BENETTI, S
    FERRETTI, V
    POLLINI, GP
    POLO, E
    ZANIRATO, V
    TETRAHEDRON, 1989, 45 (05) : 1517 - 1532
  • [7] A NEW SYNTHETIC ROUTE TO (+/-)-FORSKOLIN
    BEGLEY, MJ
    CHESHIRE, DR
    HARRISON, T
    HUTCHINSON, JH
    MYERS, PL
    PATTENDEN, G
    TETRAHEDRON, 1989, 45 (16) : 5215 - 5246
  • [8] Expedient Construction of the Ziegler Intermediate Useful for the Synthesis of Forskolin via Consecutive Rearrangements
    Ye, Heping
    Deng, Gang
    Liu, Jun
    Qiu, Fayang G.
    ORGANIC LETTERS, 2009, 11 (23) : 5442 - 5444
  • [9] A SYNTHETIC APPROACH TO RING-B OF FORSKOLIN
    RAZMILIC, I
    LOPEZ, J
    CORTES, M
    SYNTHETIC COMMUNICATIONS, 1993, 23 (08) : 1155 - 1173
  • [10] A SYNTHETIC APPROACH TO THE AB-RING SYSTEM OF FORSKOLIN
    KULKARNI, YS
    SNIDER, BB
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1986, 18 (1-2) : 7 - 10
12345