Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB spiroacetal

被引：37

作者：

Vellucci, Danielle ^{[1
]}

Rychnovsky, Scott D. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 04期

关键词：

D O I：

10.1021/ol0630447

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity.

引用

页码：711 / 714

页数：4

共 31 条

[1] Nonanomerlc spiroketals in natural products: Structures, sources, and synthetic strategies [J].

Aho, JE ;

Pihko, PM ;

Rissa, TK .

CHEMICAL REVIEWS, 2005, 105 (12) :4406-4440

[2]

Amano S, 1997, SYNLETT, P1300

[3]

Awakura D, 2000, SYNLETT, P1733

[4] Pectenotoxin-2 synthetic studies. 2. Construction and conjoining of ABC and DE eastern hemisphere subtargets [J].

Bondar, D ;

Liu, J ;

Muller, T ;

Paquette, LA .

ORGANIC LETTERS, 2005, 7 (09) :1813-1816

[5] Chemistry of bis-spiroacetal systems: Natural products, synthesis and stereochemistry [J].

Brimble, MA ;

Furkert, DP .

CURRENT ORGANIC CHEMISTRY, 2003, 7 (14) :1461-1484

[6] Oocyte-based screening of cytokinesis inhibitors and identication of pectenotoxin-2 that induces Bim/Bax-mediated apoptosis in p53-deficient tumors [J].

Chae, HD ;

Choi, TS ;

Kim, BM ;

Jung, JH ;

Bang, YJ ;

Shin, DY .

ONCOGENE, 2005, 24 (30) :4813-4819

[7] An aldol approach to the synthesis of the EF fragment of spongistatin 1 [J].

Crimmins, MT ;

Katz, JD ;

McAtee, LC ;

Tabet, EA ;

Kirincich, SJ .

ORGANIC LETTERS, 2001, 3 (06) :949-952

[8] Structures of new pectenotoxin analogs, pectenotoxin-2 seco acid and 7-epi-pectenotoxin-2 seco acid, isolated from a dinoflagellate and greenshell mussels [J].

Daiguji, M ;

Satake, M ;

James, KJ ;

Bishop, A ;

MacKenzie, L ;

Naoki, H ;

Yasumoto, T .

CHEMISTRY LETTERS, 1998, (07) :653-654

[9]

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

[10]

2-S

← 1 2 3 4 →