Synthesis of the integrastatin nucleus using the Ramberg-Bilcklund reaction

被引：31

作者：

Foot, JS ^{[1
]}

Giblin, GMP

Taylor, RJK

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] GlaxoSmithKline, Dept Med Chem Neurol, Welwyn Garden City AL6 9AR, Herts, England

[3] GlaxoSmithKline, GI CEDD, Welwyn Garden City AL6 9AR, Herts, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

关键词：

D O I：

10.1021/ol035786v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of the tetracyclic nucleus of the Integrastatins, natural products that have been shown to selectively inhibit HIV-1 integrase, is reported. Key steps of this synthesis involve a novel cis-selective Ramberg-Backlund reaction and an unusual Lewis acid-promoted cyclization step.

引用

页码：4441 / 4444

页数：4

共 14 条

[1] ALCEVAZ L, 1999, TETRAHEDRON, V55, P3707
[2] Casy G., 2003, ORG REACTIONS, V62, P357
[3] *CCDC, 219622 CCDC
[4] A NEW ONE-FLASK RAMBERG-BACKLUND REACTION
CHAN, TL
FONG, S
LI, Y
MAN, TO
POON, CD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (15) : 1771 - 1772
[5] TERT-BUTYL HYDROPEROXIDE PYRIDINIUM DICHROMATE - A CONVENIENT REAGENT SYSTEM FOR ALLYLIC AND BENZYLIC OXIDATIONS
CHIDAMBARAM, N
CHANDRASEKARAN, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) : 5048 - 5051
[6] TIN(II) CHLORIDE DIHYDRATE - A MILD AND EFFICIENT REAGENT FOR CLEAVING ACETALS
FORD, KL
ROSKAMP, EJ
[J]. TETRAHEDRON LETTERS, 1992, 33 (09) : 1135 - 1138
[7] The first synthesis of the epoxide-containing macrolactone nucleus of oximidine I
Harvey, JE
Raw, SA
Taylor, RJK
[J]. TETRAHEDRON LETTERS, 2003, 44 (38) : 7209 - 7212
[8] LOW-VALENT TITANIUM - A NEW APPROACH TO DEPROTECTION OF ALLYL AND BENZYL GROUPS
KADAM, SM
NAYAK, SK
BANERJI, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (35) : 5129 - 5132
[9] A formal total synthesis of (+)-apicularen A: base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products
Lewis, A
Stefanuti, I
Swain, SA
Smith, SA
Taylor, RJK
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (01) : 104 - 116
[10] IONIC REACTIONS OF CARBON TETRACHLORIDE . SURVEY OF REACTIONS WITH KETONES, ALCOHOLS, AND SULFONES
MEYERS, CY
MALTE, AM
MATTHEWS, WS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (26) : 7510 - &

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