An aldol approach to the synthesis of the EF fragment of spongistatin 1

被引：41

作者：

Crimmins, MT ^{[1
]}

Katz, JD ^{[1
]}

McAtee, LC ^{[1
]}

Tabet, EA ^{[1
]}

Kirincich, SJ ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 06期

关键词：

D O I：

10.1021/ol015652m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A synthesis of the C29-C51 fragment of spongistatin 1, containing the E and F rings, has been completed. The approach relies on four diastereoselective aldol additions and an asymmetric glycolate alkylation to establish eight of the eleven stereogenic centers. The intact chlorodiene side chain was appended by a Lewis acid catalyzed addition of an allylstannane to an epoxy enol ether.

引用

页码：949 / 952

页数：4

共 58 条

[1] Asymmetric synthesis of the F-pyran fragment of the altohyrtins [J].

Anderson, JC ;

McDermott, BP .

TETRAHEDRON LETTERS, 1999, 40 (39) :7135-7138

[2] Synthesis of the C1-C28 portion of spongistatin 1 (altohyrtin A) [J].

Claffey, MM ;

Hayes, CJ ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8267-8274

[3] A method for constructing the C2-C12 dispiroacetal moiety of altohyrtin A [J].

Claffey, MM ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7646-7647

[4] Synthesis of the C16-C28 spiroketal subunit of spongistatin 1 (altohyrtin A): The pyrone approach [J].

Crimmins, MT ;

Katz, JD .

ORGANIC LETTERS, 2000, 2 (07) :957-960

[5] Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].

Crimmins, MT ;

King, BW ;

Tabet, EA ;

Chaudhary, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902

[6] Synthesis of the AB spiroketal subunit of spongistatin 1 (altohyrtin A): The pyrone approach [J].

Crimmins, MT ;

Washburn, DG .

TETRAHEDRON LETTERS, 1998, 39 (41) :7487-7490

[7] Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones: Dependence of selectivity on amine base and Lewis acid stoichiometry [J].

Crimmins, MT ;

King, BW ;

Tabet, EA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) :7883-7884

[8] An improved synthetic preparation of 3-butenal [J].

Crimmins, MT ;

Kirincich, SJ ;

Wells, AJ ;

Choy, AL .

SYNTHETIC COMMUNICATIONS, 1998, 28 (19) :3675-3679

[9] An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin [J].

Crimmins, MT ;

Choy, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5653-5660

[10] Asymmetric total synthesis of (+)-milbemycin D [J].

Crimmins, MT ;

Alawar, RS ;

Vallin, IM ;

Hollis, WG ;

OMahony, R ;

Lever, JG ;

BankaitisDavis, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7513-7528

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