Highly functionalized pyranopyrans from furans: A synthesis of the C27-C38 and C44-C53 subunits of norhalichondrin B

被引：47

作者：

Henderson, James A. ^{[1
]}

Jackson, Katrina L. ^{[1
]}

Phillips, Andrew J. ^{[1
]}

机构：

[1] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 25期

关键词：

D O I：

10.1021/ol702559e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.

引用

页码：5299 / 5302

页数：4

共 50 条

[1] TOTAL SYNTHESIS OF HALICHONDRIN-B AND NORHALICHONDRIN-B [J].

AICHER, TD ;

BUSZEK, KR ;

FANG, FG ;

FORSYTH, CJ ;

JUNG, SH ;

KISHI, Y ;

MATELICH, MC ;

SCOLA, PM ;

SPERO, DM ;

YOON, SK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3162-3164

[2] SYNTHETIC STUDIES TOWARDS HALICHONDRINS - SYNTHESIS OF THE C.27-C.38 SEGMENT [J].

AICHER, TD ;

BUSZEK, KR ;

FANG, FG ;

FORSYTH, CJ ;

JUNG, SH ;

KISHI, Y ;

SCOLA, PM .

TETRAHEDRON LETTERS, 1992, 33 (12) :1549-1552

[3] SYNTHETIC STUDIES TOWARDS HALICHONDRINS [J].

AICHER, TD ;

KISHI, Y .

TETRAHEDRON LETTERS, 1987, 28 (30) :3463-3466

[4] Halichondrin B: synthesis of the C(37)-C(54) subunit [J].

Austad, BC ;

Hart, AC ;

Burke, SD .

TETRAHEDRON, 2002, 58 (10) :2011-2026

[5] ENANTIOSELECTIVE SYNTHESIS OF A HALICHONDRIN-B C(20)-]C(36) PRECURSOR [J].

BURKE, SD ;

ZHANG, G ;

BUCHANAN, JL .

TETRAHEDRON LETTERS, 1995, 36 (39) :7023-7026

[6] SYNTHESIS OF A C(22)-]C(34) HALICHONDRIN PRECURSOR VIA A DOUBLE DIOXANONE-TO-DIHYDROPYRAN REARRANGEMENT [J].

BURKE, SD ;

BUCHANAN, JL ;

ROVIN, JD .

TETRAHEDRON LETTERS, 1991, 32 (32) :3961-3964

[7] An expeditious synthesis of the C(38)-C(54) halichondrin B subunit [J].

Burke, SD ;

Austad, BC ;

Hart, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6770-6771

[8] Synthesis of a C(22)-C(34) halichondrin B precursor via ring opening double ring closing metathesis [J].

Burke, SD ;

Quinn, KJ ;

Chen, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8626-8627

[9] AN EXPEDITIOUS SYNTHESIS OF THE C(1)-C(14) SUBUNIT OF HALICHONDRIN-B [J].

BURKE, SD ;

JUNG, KW ;

PHILLIPS, JR ;

PERRI, RE .

TETRAHEDRON LETTERS, 1994, 35 (05) :703-706

[10] Halichondrin B: Synthesis of the C(1)-C(15) subunit [J].

Burke, SD ;

Jung, KW ;

Lambert, WT ;

Phillips, JR ;

Klovning, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13) :4070-4087

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