CHEMISTRY OF PSEUDOMONIC ACID .2. CONVERSION OF PSEUDOMONIC ACID-A INTO MONIC ACID-A AND ITS ESTERS

被引：42

作者：

CLAYTON, JP

LUK, K

ROGERS, NH

机构：

[1] Beecham Pharmaceutical, Research Division, Betchworth, Surrey RH3 7AJ, Brockham Park

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 02期

关键词：

D O I：

10.1039/p19790000308

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By suitable protection and deprotection, the 9-hydroxynonanoic acid side-chain of pseudomonic acid A (1a), a naturally occurring antibiotic, was cleaved in a highly efficient one-pot reaction to the allylic acid (3a), 4-[5S-(2S,3S-epoxy-5S-hydroxy-4S-methylhexyl)-3R,4H-dihydroxytetrahydropyran-2S- yl]-3-methylbut-2(E)-enoic acid. We have ascribed the trivial name, monic acid A, to this allylic acid. Esters of monic acid A were readily prepared from the free acid (3a) and also from the ketone (2) which could be condensed with phosphonoacetates.

引用

页码：308 / 313

页数：6

共 15 条

[1] CHEMISTRY OF PSEUDOMONIC ACID .1. ABSOLUTE-CONFIGURATION OF PSEUDOMONIC ACID-A
ALEXANDER, RG
CLAYTON, JP
LUK, K
ROGERS, NH
KING, TJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (06): : 561 - 565
[2] STRUCTURE OF PSEUDOMONIC ACID, AN ANTIBIOTIC FROM PSEUDOMONAS-FLUORESCENS
CHAIN, EB
MELLOWS, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (20) : 847 - 848
[3] PSEUDOMONIC ACID .1. STRUCTURE OF PSEUDOMONIC-ACID-A - NOVEL ANTIBIOTIC PRODUCED BY PSEUDOMONAS-FLUORESCENS
CHAIN, EB
MELLOWS, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (03): : 294 - 309
[4] DEWOLFE RH, 1975, SYNTHESIS, P153
[5] SYNTHESIS OF OLIGORIBONUCLEOTIDES .4. PREPARATION OF DINUCLEOSIDE PHOSPHATES FROM 2',5'-PROTECTED RIBONUCLEOSIDE DERIVATIVES
GRIFFIN, BE
JARMAN, M
REESE, CB
[J]. TETRAHEDRON, 1968, 24 (02) : 639 - &
[6] SYNTHESIS OF OLIGORIBONUCLEOTIDES .2. METHOXYMETHYLIDENE DERIVATIVES OF RIBONUCLEOSIDES AND 5'-RIBONUCLEOTIDES
GRIFFIN, BE
JARMAN, M
REESE, CB
SULSTON, JE
[J]. TETRAHEDRON, 1967, 23 (05) : 2301 - &
[7] Experiments on the synthesis of 1-methylcyclohexylidene-4-acetic acid. Part II
Harding, Victor John
Haworth, Walter Norman
Perkin, William Henry, Jr.
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1908, 93 : 1943 - 1975
[8] JARMAN M, 1964, CHEM IND-LONDON, P1493
[9] THE CONVERSION OF ALKYL HALIDES TO THE NEXT HIGHER HOMOLOGOUS PHOSPHONATES
MAGERLEIN, BJ
KAGAN, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) : 593 - 596
[10] MALEVANNAYA RA, 1971, ZH OBSHCH KHIM+, V41, P1426

← 1 2 →