An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate

被引：18

作者：

Almstead, JIK ^{[1
]}

Demuth, TP ^{[1
]}

Ledoussal, B ^{[1
]}

机构：

[1] Procter & Gamble Pharmaceut, Hlth Care Res Ctr, Mason, OH 45040 USA

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 18期

关键词：

D O I：

10.1016/S0957-4166(98)00349-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C-8 position. A palladium-mediated carbonylation reaction was employed to generate the key alpha,beta-unsaturated dialdehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3179 / 3183

页数：5

共 50 条

[31] Stereoselective total synthesis of bistramide A
Yadav, J. S.
Chetia, Lakshindra
ORGANIC LETTERS, 2007, 9 (22) : 4587 - 4589
[32] Stereoselective total synthesis of (+)-synargentolide A
Prasad, Kavirayani R.
Penchalaiah, Kamala
TETRAHEDRON-ASYMMETRY, 2010, 21 (23) : 2853 - 2858
[33] Stereoselective total synthesis of almorexant
Reddy, N. Siva Senkar
Reddy, B. V. Subba
TETRAHEDRON LETTERS, 2014, 55 (20) : 3157 - 3159
[34] A Stereoselective Total Synthesis of Verbalactone
Das, Biswanath
Laxminarayana, Keetha
Krishnaiah, Martha
Kumar, Duddukuri Nandan
HELVETICA CHIMICA ACTA, 2009, 92 (09) : 1840 - 1844
[35] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-ISOCELORBICOL
HUFFMAN, JW
RAVEENDRANATH, PC
TETRAHEDRON, 1987, 43 (23) : 5557 - 5565
[36] STEREOSELECTIVE TOTAL SYNTHESIS OF BAZZANENE
KODAMA, M
TAKAHASHI, T
KURIHARA, T
ITO, S
TETRAHEDRON LETTERS, 1980, 21 (29) : 2811 - 2812
[37] A stereoselective total synthesis of (±)-tormesol
Kim, Hyoungsu
Bae, Hoon
Kim, Sanghee
Kim, Deukjoon
Lee, Dongjoo
Paton, Robert S.
TETRAHEDRON, 2011, 67 (51) : 10017 - 10025
[38] Stereoselective total synthesis of (+)-sedamine
Borah, JC
Boruwa, J
Barua, NC
LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (02) : 140 - 142
[39] Stereoselective Total Synthesis of (-)-Kumausallene
Werness, Jenny B.
Tang, Weiping
ORGANIC LETTERS, 2011, 13 (14) : 3664 - 3666
[40] Stereoselective total synthesis of chrysanthemol
Mou, LY
Zhu, LY
Lin, ZY
Liang, XT
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2001, 3 (02) : 103 - 116

← 1 2 3 4 5 →