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 45 条

[31] SYNTHESIS OF MACROLIDE ANTIBIOTICS .16. SYNTHESIS OF ERYTHRONOLIDES A AND B BY A COUPLING SCHEME OF (C5-C9) + (C3-C4) + (C1-C2) + (C10) + (C-11-C-13) FRAGMENTS AND SYNTHESIS OF THE C5-C9 FRAGMENT
SVIRIDOV, AF
BORODKIN, VS
ERMOLENKO, MS
YASHUNSKII, DV
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (03): : 600 - 606
[32] Synthesis of the C-1-C-10 fragment of the macrolide antibiotic Nystatin A(1) from a chiral building block obtained via chemoenzymatic approach
Bonini, C
Giugliano, A
Racioppi, R
Righi, G
TETRAHEDRON LETTERS, 1996, 37 (14) : 2487 - 2490
[33] TOTAL SYNTHESIS OF AVERMECTINS .2. ENANTIOSELECTIVE SYNTHESIS OF THE C10-C25 NORTHERN FRAGMENT AND FINAL STEPS FOR THE CONSTRUCTION OF THE 22,23-DIHYDROAVERMECTIN B1B AGLYCONE
FEREZOU, JP
JULIA, M
LI, Y
LIU, LW
PANCRAZI, A
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1995, 132 (04): : 428 - 452
[34] Stereoselective total synthesis of C2-symmetric natural products pyrenophorol and its derivatives
Narala, Siva Ganesh
Nagalatha, G.
Venkat Narsaiah, A.
NATURAL PRODUCT RESEARCH, 2020, 34 (15) : 2173 - 2178
[35] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .14. HIGHLY STEREOSELECTIVE TOTAL SYNTHESIS OF TYLONOLIDE, THE AGLYCON OF THE 16-MEMBERED MACROLIDE ANTIBIOTIC TYLOSIN .1. CONSTRUCTION OF THE C-1-C-8 CHIRAL CENTERS
TANAKA, T
OIKAWA, Y
HAMADA, T
YONEMITSU, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1987, 35 (06) : 2209 - 2218
[36] Double diastereoselection in aldol reactions mediated by dicyclohexylchloroborane between chiral aldehydes and a chiral ethyl ketone derived from L-erythrulose.: Synthesis of a C1-C9 fragment of the structure of the antifungal metabolite Soraphen A1 α
Díaz-Oltra, S
Murga, J
Falomir, E
Carda, M
Peris, G
Marco, JA
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (20): : 8130 - 8139
[37] Total synthesis of antibiotic, micrococcin P, from 2,3,6-polythiazolesubstituted pyridine skeleton [fragment A-C]
Shin, C
Okumura, K
Shigekuni, M
Nakamura, Y
CHEMISTRY LETTERS, 1998, (02) : 139 - 140
[38] Total synthesis of zoanthamine alkaloids .2. Construction of the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of zoanthamine
Tanner, D
Tedenborg, L
Somfai, P
ACTA CHEMICA SCANDINAVICA, 1997, 51 (12): : 1217 - 1223
[39] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .22. A STEREOSELECTIVE TOTAL SYNTHESIS OF (9S)-9-DIHYDROERYTHRONOLIDE A VIA COUPLING BETWEEN THE RIGHT-HALF (C1-C6) ALDEHYDE AND THE LEFT-HALF (C7-C15) SULFOXIDE
TONE, H
NISHI, T
OIKAWA, Y
HIKOTA, M
YONEMITSU, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (05) : 1167 - 1172
[40] Total synthesis of avermectins. Part 2: Enantioselective synthesis of the C10-C25 northern fragment and final steps for the construction of the 22,23-dihydroavermectin B1b aglycone
Bull Soc Chim Fr, 4 (428):

← 1 2 3 4 5 →