Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1-C19 Sector

被引：30

作者：

Joyasawal, Sipak ^{[1
]}

Lotesta, Stephen D. ^{[1
]}

Akhmedov, N. G. ^{[2
]}

Williams, Lawrence J. ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Biol Chem, Piscataway, NJ 08854 USA

[2] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

关键词：

ASYMMETRIC EPOXIDATION; ALLENE EPOXIDATION; PART II; FRAGMENT; EFFICIENT; ALCOHOLS; CYCLIZATION; SUBUNIT; KETONES; SYSTEM;

D O I：

10.1021/ol902984e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented, The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.

引用

页码：988 / 991

页数：4

共 45 条

[1] Synthetic studies toward pectenotoxin 2.: Part I.: Stereocontrolled access to the C10-C22 fragment [J].

Aho, Jatta E. ;

Salomaki, Elina ;

Rissanen, Karl ;

Pihko, Petri M. .

ORGANIC LETTERS, 2008, 10 (19) :4179-4182

[2] A Novel Approach to the CDE Ring System of Pectenotoxin-4 Triggered by VO(acaC)2-Induced Epoxy-Acetalization [J].

Carley, Sarah ;

Brimble, Margaret A. .

ORGANIC LETTERS, 2009, 11 (03) :563-566

[3] An efficient method for removal of ruthenium byproducts from olefin metathesis reactions [J].

Cho, JH ;

Kim, BM .

ORGANIC LETTERS, 2003, 5 (04) :531-533

[4] ALLENE EPOXIDATION - OXIDATIVE CYCLIZATIONS OF ALLENYL ALCOHOLS [J].

CRANDALL, JK ;

BATAL, DJ .

TETRAHEDRON LETTERS, 1988, 29 (38) :4791-4794

[5] ALLENE EPOXIDATION - HIGHLY FUNCTIONALIZED TETRAHYDROFURANS AND TETRAHYDROPYRANS FROM THE OXIDATIVE CYCLIZATION OF ALLENIC ALCOHOLS [J].

CRANDALL, JK ;

BATAL, DJ ;

LIN, F ;

REIX, T ;

NADOL, GS ;

NG, RA .

TETRAHEDRON, 1992, 48 (08) :1427-1448

[6]

Evans DA, 2002, ANGEW CHEM INT EDIT, V41, P4573, DOI 10.1002/1521-3773(20021202)41:23<4573::AID-ANIE4573>3.0.CO

[7]

2-S

[8]

Evans DA, 2002, ANGEW CHEM INT EDIT, V41, P4569, DOI 10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO

[9]

2-V

[10] Synthesis of the C8-C20 and C21-C30 segments of pectenotoxin 2 [J].

Fujiwara, Kenshu ;

Aki, Yu-ichi ;

Yamamoto, Fuyuki ;

Kawamura, Mariko ;

Kobayashi, Masanori ;

Okano, Azusa ;

Awakura, Daisuke ;

Shiga, Shunsuke ;

Murai, Akio ;

Kawai, Hidetoshi ;

Suzuki, Takanori .

TETRAHEDRON LETTERS, 2007, 48 (26) :4523-4527

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