Synthetic studies on spongistatins: synthesis of the C29-C44 fragment

被引：22

作者：

Samadi, M ^{[1
]}

Munoz-Letelier, C ^{[1
]}

Poigny, S ^{[1
]}

Guyot, M ^{[1
]}

机构：

[1] Museum Natl Hist Nat, CNRS, Lab Chim Subst Nat, F-75005 Paris, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)00383-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent synthesis of the C29-C44 fragment, the common subunit of the spongipyran macrolides is described. The key step of the synthesis is the C-glycosidation reaction which is based on coupling of the lithiated F-ring sulfone with the E-ring aldehyde, and subsequent reductive desulfonylation to afford the E-F bis (pyran) with high stereoselectivity at the anomeric carbon. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3349 / 3353

页数：5

共 50 条

[1] Synthetic studies on altohyrtins (spongistatins): synthesis of the C29-C44 (EF) portion
Terauchi, T
Morita, M
Kimijima, K
Nakamura, Y
Hayashi, G
Tanaka, T
Kanoh, N
Nakata, M
[J]. TETRAHEDRON LETTERS, 2001, 42 (32) : 5505 - 5508
[2] Synthesis of the C29-C44 portion of spongistatin 1 (altohyrtin A)
Wallace, GA
Scott, RW
Heathcock, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13): : 4145 - 4152
[3] Synthetic Studies on Altohyrtins (Spongistatins): Synthesis of the C1-C14 (AB) Spiroacetal Portion
[J]. Tetrahedron Lett, 22 (3795):
[4] Synthetic Studies toward the C14-C29 Fragment of Mirabalin
Cornil, Johan
Echeverria, Pierre-Georges
Reymond, Sebastien
Phansavath, Phannarath
Ratovelomanana-Vidal, Virginie
Guerinot, Amandine
Cossy, Janine
[J]. ORGANIC LETTERS, 2016, 18 (18) : 4534 - 4537
[5] SYNTHETIC STUDY OF SALINOMYCIN (SYNTHESIS OF C-18-C-29 FRAGMENT)
HORITA, K
NAGATO, S
OIKAWA, Y
YONEMITSU, O
[J]. HETEROCYCLES, 1986, 24 (01) : 277 - 277
[6] Synthetic studies on altohyrtins (spongistatins): synthesis of the C15-C28 (CD) spiroacetal portion
Terauchi, T
Terauchi, T
Sato, I
Tsukada, T
Kanoh, N
Nakata, M
[J]. TETRAHEDRON LETTERS, 2000, 41 (15) : 2649 - 2653
[7] Synthetic studies on altohyrtins (Spongistatins): Synthesis of the C1-C14 (AB) spiroacetal portion
Terauchi, T
Nakata, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (22) : 3795 - 3798
[8] Synthetic approaches towards laulimalide:: Synthesis of the C12-C29 fragment
Shimizu, A
Nishiyama, S
[J]. SYNLETT, 1998, (11) : 1209 - +
[9] Studies on the total synthesis of sanglifehrin A: stereoselective synthesis of the C(29)-C(39) fragment
Dias, LC
Salles, AG
[J]. TETRAHEDRON LETTERS, 2006, 47 (13) : 2213 - 2216
[10] Studies towards the synthesis of the C29-C51 fragment of altohyrtin A
Fernandez-Megia, E
Gourlaouen, N
Ley, SV
Rowlands, GJ
[J]. SYNLETT, 1998, (09) : 991 - +

← 1 2 3 4 5 →