A symmetry-based formal synthesis of Zaragozic acid A

被引：22

作者：

Freeman-Cook, KD ^{[1
]}

Halcomb, RL ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 19期

关键词：

D O I：

10.1021/jo000665j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A symmetry-based strategy for the synthesis of the zaragozic acids is reported. Two enantioselective dihydroxylations were used to establish the absolute configuration of a C-2 symmetric intermediate. Noteworthy transformations include a group-selective lactonization, which accomplished an end-differentiation of a pseudo-C-2 symmetric intermediate. Late stage protecting group adjustments and oxidations accomplished a formal synthesis of zaragozic acid A.

引用

页码：6153 / 6159

页数：7

共 49 条

[1] Total synthesis of (+)-zaragozic acid C [J].

Armstrong, A ;

Jones, LH ;

Barsanti, PA .

TETRAHEDRON LETTERS, 1998, 39 (20) :3337-3340

[2]

BALKRISHNA SB, 1981, TETRAHEDRON, V37, P2091

[3]

BAXTER A, 1992, J BIOL CHEM, V267, P11705

[4] ZARAGOZIC ACIDS - A FAMILY OF FUNGAL METABOLITES THAT ARE PICOMOLAR COMPETITIVE INHIBITORS OF SQUALENE SYNTHASE [J].

BERGSTROM, JD ;

KURTZ, MM ;

REW, DJ ;

AMEND, AM ;

KARKAS, JD ;

BOSTEDOR, RG ;

BANSAL, VS ;

DUFRESNE, C ;

VANMIDDLESWORTH, FL ;

HENSENS, OD ;

LIESCH, JM ;

ZINK, DL ;

WILSON, KE ;

ONISHI, J ;

MILLIGAN, JA ;

BILLS, G ;

KAPLAN, L ;

OMSTEAD, MN ;

JENKINS, RG ;

HUANG, L ;

MEINZ, MS ;

QUINN, L ;

BURG, RW ;

KONG, YL ;

MOCHALES, S ;

MOJENA, M ;

MARTIN, I ;

PELAEZ, F ;

DIEZ, MT ;

ALBERTS, AW .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) :80-84

[5] Preparation of the zaragozic acid core through the rearrangement of an oxonium ylide [J].

Brogan, JB ;

Zercher, CK .

TETRAHEDRON LETTERS, 1998, 39 (13) :1691-1694

[6] Orthoester condensation/C-O insertion reaction sequence for the preparation of tetrahydrofurans [J].

Calter, MA ;

Sugathapala, PM .

TETRAHEDRON LETTERS, 1998, 39 (48) :8813-8816

[7] Total synthesis of zaragozic acid A (squalestatin S1). Synthesis of the relay compound [J].

Caron, S ;

Stoermer, D ;

Mapp, AK ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9126-9134

[8] (+)-ZARAGOZIC-ACID-C - SYNTHESIS AND RELATED STUDIES [J].

CARREIRA, EM ;

DUBOIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8106-8125

[9] [4,5-C] FUROTROPONE - A NEW HETEROCYCLIC SYSTEM [J].

COOK, MJ ;

FORBES, EJ .

TETRAHEDRON, 1968, 24 (12) :4501-&

[10] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

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