EFFICIENT TOTAL SYNTHESIS OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77

被引：97

作者：

HAMADA, Y

HARA, O

KAWAI, A

KOHNO, Y

SHIOIRI, T

机构：

[1] Faculty of Pharmaceutical Sciences, Nagoya City University Tanabe-dori, Mizuho-ku, Nagoya

来源：

TETRAHEDRON | 1991年 / 47卷 / 40期

关键词：

AI-77-B; DIHYDROISOCOUMARIN; HYDROXY AMINO ACID; STEREOSELECTIVE OSMYLATION; INTRAMOLECULAR PINNER REACTION;

D O I：

10.1016/S0040-4020(01)82406-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

First total synthesis of AI-77-B (1), a gastroprotective substance from Bacillus pumilus AI-77, was achieved in a stereoselective and convergent manner. In this synthesis, the dihydroisocoumarin part 2 was constructed in one step through 1,2-addition of the benzylic anion 17b to Boc-L-leucinal 7b. The hydroxy amino acid 4 was elaborated from (R)-glutamic acid in a highly stereoselective manner. Condensation of 2.HCl and 4, intramolecular Pinner reaction, followed by mild hydrolysis afforded AI-77-B (1).

引用

页码：8635 / 8652

页数：18

共 20 条

[1] STEREOSELECTIVE SYNTHESIS OF THE HYDROXY AMINO-ACID MOIETY OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77
KAWAI, A
HARA, O
HAMADA, Y
SHIOIRI, T
TETRAHEDRON LETTERS, 1988, 29 (48) : 6331 - 6334
[2] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .83. STEREOSELECTIVE TOTAL SYNTHESIS OF AI-77-B, A GASTROPROTECTIVE SUBSTANCE FROM BACILLUS-PUMILUS AI-77
HAMADA, Y
KAWAI, A
KOHNO, Y
HARA, O
SHIOIRI, T
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) : 1524 - 1525
[3] TOTAL SYNTHESIS OF THE GASTROPROTECTIVE SUBSTANCE AI-77-B AND OF ANALOGS
DURGNAT, JM
VOGEL, P
HELVETICA CHIMICA ACTA, 1993, 76 (01) : 222 - 240
[4] TOTAL SYNTHESIS OF AI-77-B
BROADY, SD
REXHAUSEN, JE
THOMAS, EJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (10) : 708 - 710
[5] Total synthesis of AI-77-B
Rao, Maddimsetti Venkateswara
Rao, Batchu Venkateswara
Ramesh, Bokka
TETRAHEDRON LETTERS, 2014, 55 (43) : 5921 - 5924
[6] Asymmetric total synthesis of the gastroprotective microbial agent AI-77-B
Ghosh, AK
Bischoff, A
Cappiello, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (05) : 821 - 832
[7] A new enantioselective total synthesis of AI-77-B
Kotsuki, H
Araki, T
Miyazaki, A
Iwasaki, M
Datta, PK
ORGANIC LETTERS, 1999, 1 (03) : 499 - 502
[8] Studies toward a synthesis of AI-77-B
Davies, G
Russell, AT
TETRAHEDRON LETTERS, 2002, 43 (47) : 8519 - 8522
[9] A TOTAL SYNTHESIS OF THE NATURAL ENANTIOMER OF THE GASTROPROTECTIVE NATURAL-PRODUCTS AI-77-B AND AMICOUMACIN-C HYDROCHLORIDE
WARD, RA
PROCTER, G
TETRAHEDRON, 1995, 51 (45) : 12301 - 12318
[10] Total synthesis of AI-77-B: stereoselective hydroxylation of 4-alkenylazetidinones
Broady, SD
Rexhausen, JE
Thomas, EJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08): : 1083 - 1094

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