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
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
  • [31] Cyclization and Cycloisomerization of π-Tethered Ynamides: An Expedient Synthetic Method to Construct Carbo- and Heterocycles
    Prabagar, B.
    Ghosh, Nayan
    Sahoo, Akhila K.
    SYNLETT, 2017, 28 (19) : 2539 - 2555
  • [32] An expedient "click' approach for the synthetic evaluation of ester-triazole-tethered organosilica conjugates
    Singh, Gurjaspreet
    Rani, Sunita
    APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (02)
  • [33] Synthetic studies of forskolin.: A formal synthesis via a Nicolaou's advanced intermediate
    Liu, HJ
    Shang, X
    HETEROCYCLES, 1999, 50 (02) : 1105 - 1113
  • [34] Synthetic studies of forskolin. A Diels-Alder approach to Corey's endoperoxide
    Liu, HJ
    Shang, X
    HETEROCYCLES, 1997, 44 : 143 - 147
  • [35] AN EXPEDIENT SYNTHETIC APPROACH TO THE PHYSOSTIGMINE ALKALOIDS VIA INTRAMOLECULAR FORMAMIDINE YLIDE CYCLO-ADDITIONS
    SMITH, R
    LIVINGHOUSE, T
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09): : 1554 - 1555
  • [36] TRANSFORMATION OF YEAST DIRECTLY WITH SYNTHETIC OLIGONUCLEOTIDES
    MOERSCHELL, RP
    DAS, G
    SHERMAN, F
    METHODS IN ENZYMOLOGY, 1991, 194 : 362 - 369
  • [37] TRANSFORMATION OF HEXOSES ON NATURAL AND SYNTHETIC ZEOLITES
    Patrylak, Lyubov
    Konovalov, Serhii
    Zubenko, Stepan
    Yakovenko, Anzhela
    CHEMISTRY & CHEMICAL TECHNOLOGY, 2023, 17 (02): : 287 - 293
  • [38] BILINEAR TRANSFORMATION BY SYNTHETIC DIVISION - COMMENTS
    MALVAR, HS
    IEEE TRANSACTIONS ON AUTOMATIC CONTROL, 1985, 30 (04) : 416 - 416
  • [39] A new synthetic approach to forskolin: Construction of the ABC ring system from D-galactose
    Hanna, I
    Wlodyka, P
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20): : 6985 - 6990
  • [40] 6-ENDO-TRIG RADICAL CYCLIZATIONS - SYNTHETIC APPROACHES TO THE A-B-RING OF (+/-)-FORSKOLIN
    ANIES, C
    BILLOT, L
    LALLEMAND, JY
    PANCRAZI, A
    TETRAHEDRON LETTERS, 1995, 36 (40) : 7247 - 7250