CHIRAL SYNTHESIS OF POLYKETIDE-NATURAL PRODUCTS .40. TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LYSOCELLIN .2. STEREOCONTROLLED SYNTHESIS OF THE C10-C23 FRAGMENT AND ITS ALDOL CONDENSATION WITH THE C1-C9 FRAGMENT TO COMPLETE THE TOTAL SYNTHESIS OF LYSOCELLIN

被引：6

作者：

HORITA, K ^{[1
]}

TANAKA, K ^{[1
]}

INOUE, T ^{[1
]}

YONEMITSU, O ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 38期

关键词：

POLYETHER ANTIBIOTIC; TOTAL SYNTHESIS; ALDOL REACTION; STEREOCONTROLLED SYNTHESIS;

D O I：

10.1016/S0040-4039(00)61140-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-10-C23 ethyl ketone (4) was synthesized via coupling of the C-16-C23 aldehyde (3) with the C-11-C-15 fragment (8), and subjected to the aldol reaction with the C1-C-9 aldehyde (2) to complete the first stereoselective total synthesis of the polyether antibiotic lysocellin (1).

引用

页码：5541 / 5544

页数：4

共 9 条

[1] SYNTHETIC STUDIES IN THE LYSOCELLIN FAMILY OF POLYETHER ANTIBIOTICS - THE TOTAL SYNTHESIS OF FERENSIMYCIN-B
EVANS, DA
POLNIASZEK, RP
DEVRIES, KM
GUINN, DE
MATHRE, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) : 7613 - 7630
[2] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS
HORITA, K
YOSHIOKA, T
TANAKA, T
OIKAWA, Y
YONEMITSU, O
[J]. TETRAHEDRON, 1986, 42 (11) : 3021 - 3028
[3] HORITA K, IN PRESS TETRAHEDRON
[4] LANDSBURG PT, 1974, J AM CHEM SOC, V96, P896
[5] MANCUSO AJ, 1981, SYNTHESIS-STUTTGART, P165
[6] TOTAL SYNTHESIS OF LASALOCID-A
NAKATA, T
SCHMID, G
VRANESIC, B
OKIGAWA, M
SMITHPALMER, T
KISHI, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (09) : 2933 - 2935
[7] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .33. STEREOSELECTIVE SYNTHESIS OF POLYETHER ANTIBIOTICS, LASALOCID-A AND ISOLASALOCID-A, VIA A CHELATION-CONTROLLED FORMATION OF TETRAHYDROFURAN RINGS UNDER THERMODYNAMIC CONDITIONS
NODA, I
HORITA, K
OIKAWA, Y
YONEMITSU, O
[J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6035 - 6038
[8] CHELATION OR NON-CHELATION CONTROL IN ADDITION-REACTIONS OF CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY CARBONYL-COMPOUNDS
REETZ, MT
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08): : 556 - 569
[9] STILL WC, 1980, TETRAHEDRON LETT, V21, P1031

← 1 →