Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A

被引：19

作者：

Drouet, KE ^{[1
]}

Ling, TT ^{[1
]}

Tran, HV ^{[1
]}

Theodorakis, EA ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991290v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reveromycin A (1) belongs to a family of microbial polyketides with unusual structural features and biological activities. The structure of 1 is composed of a [6,6] spiroketal core decorated with highly unsaturated side chains, As a prelude to the synthesis of 1, we present herein a short, efficient, and enantioselective synthesis of the C9-C21 fragment 5 (spiroketal core) of reveromycin A.

引用

页码：207 / 210

页数：4

共 35 条

[1] STEREOSELECTIVE, CATALYTIC REDUCTION OF L-ASCORBIC-ACID - A CONVENIENT SYNTHESIS OF L-GULONO-1,4-LACTONE
ANDREWS, GC
CRAWFORD, TC
BACON, BE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) : 2976 - 2977
[2] ISOLATION AND SYNTHESIS OF 3-HYDROXY-1 AND 4-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANES FROM THE OLIVE FLY (DACUS-OLEAE)
BAKER, R
HERBERT, RH
PARTON, AH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) : 601 - 603
[3] Asymmetric synthesis of 2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazoles
Cliff, MD
Pyne, SG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) : 1023 - 1032
[4] COREY EJ, 1972, TETRAHEDRON LETT, P3769
[5] 1,7-DIOXASPIRO[5.5]UNDECANES - AN EXCELLENT SYSTEM FOR THE STUDY OF STEREOELECTRONIC EFFECTS (ANOMERIC AND EXO-ANOMERIC EFFECTS) IN ACETALS
DESLONGCHAMPS, P
ROWAN, DD
POTHIER, N
SAUVE, T
SAUNDERS, JK
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (07): : 1105 - 1121
[6] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
[7] Enantioselective total synthesis of reveromycin B
Drouet, KE
Theodorakis, EA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) : 456 - 457
[8] POLYETHER ANTIBIOTICS SYNTHESIS - TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE IONOPHORE-A-23187
EVANS, DA
SACKS, CE
KLESCHICK, WA
TABER, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) : 6789 - 6791
[9] ACYCLIC STEREOSELECTION .9. STEREOCHEMISTRY OF THE ADDITION OF LITHIUM ENOLATES TO ALPHA-ALKOXY ALDEHYDES
HEATHCOCK, CH
YOUNG, SD
HAGEN, JP
PIRRUNG, MC
WHITE, CT
VANDERVEER, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) : 3846 - 3856
[10] Total synthesis of the serine-threonine phosphatase inhibitor microcystin-LA
Humphrey, JM
Aggen, JB
Chamberlin, AR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) : 11759 - 11770

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