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

[11] STEREOCONTROLLED OSMYLATION OF MEDIUM-RING ALKENES - SYNTHESIS OF A C1-C9 ERYTHRONOLIDE FRAGMENT
VEDEJS, E
DOLPHIN, JM
MASTALERZ, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (01) : 127 - 130
[12] Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1-C9 and C10-C24 Fragments
Sayini, Ramakrishna
Srihari, Pabbaraja
SYNTHESIS-STUTTGART, 2018, 50 (03): : 663 - 675
[13] Studies directed towards the total synthesis of polyether antibiotic ionomycin: asymmetric synthesis of fragments C(24)-C(32) and C(1)-C(23)
Yadav, J. S.
Yadav, Nagendra Nath
Reddy, B. V. Subba
TETRAHEDRON, 2015, 71 (40) : 7539 - 7549
[14] THE TOTAL SYNTHESIS OF SWINHOLIDE-A .2. A STEREOCONTROLLED SYNTHESIS OF A C-1-C-15 SEGMENT
PATERSON, I
SMITH, JD
WARD, RA
TETRAHEDRON, 1995, 51 (34) : 9413 - 9436
[15] Total synthesis of milbemycin E: Resolution of the C(1)-C(10) fragment and final assembly
Steel, PG
Mills, OS
Parmee, ER
Thomas, EJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 391 - 400
[16] Enantioselective Polyol Synthesis via the Cope Rearrangement of Chiral Aldol Products. A Synthesis of the C1-C10-Fragment of Nystatin A1
Tetrahedron Lett, 1-2 (09):
[17] Enantioselective polyol synthesis via the Cope rearrangement of chiral aldol products.: A synthesis of the C1-C10-fragment of nystatin A1
Schneider, C
Rehfeuter, M
TETRAHEDRON LETTERS, 1998, 39 (1-2) : 9 - 12
[18] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .3. STEREOCONTROLLED SYNTHESIS OF A CHIRAL FRAGMENT CORRESPONDING TO BOTH THE C-1-C-4 AND C-9-C-12 UNITS OF ERYTHROMYCIN-A FROM D-GLUCOSE
OIKAWA, Y
NISHI, T
YONEMITSU, O
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (01): : 1 - 5
[19] Studies towards the total synthesis of narbonolide: stereoselective preparation of the C1-C10 fragment
Narasimhulu, C. Prasad
Iqba, Javed
Mukkanti, Khagga
Das, Parthasarathi
TETRAHEDRON LETTERS, 2008, 49 (19) : 3185 - 3188
[20] Studies toward the total synthesis of (-)-dictyostatin: Stereoselective preparation of the C1-C10 fragment
Saibaba, Vobbalareddy
Sampath, Alwar
Mukkanti, Khagga
Iqbal, Javed
Das, Parthasarathi
SYNTHESIS-STUTTGART, 2007, (18): : 2797 - 2802

← 1 2 3 4 5 →