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

[1] Chiral synthesis of polyketide derived natural products .52. Stereoselective total synthesis of lysocellin, the representative polyether antibiotic of the lysocellin family .2. Synthesis of C10-C23 subunit via construction of two rings (B and C) and its condensation with C1-C9 subunit to achieve the total synthesis of lysocellin
Horita, K
Tanaka, K
Inoue, T
Yonemitsu, O
TETRAHEDRON, 1996, 52 (02) : 551 - 564
[2] Chiral synthesis of polyketide-derived natural products .51. Stereoselective total synthesis of lysocellin, the representative polyether antibiotic of the lysocellin family .1. Synthesis of C1-C9 and C16-C23 subunits
Horita, K
Inoue, T
Tanaka, K
Yonemitsu, O
TETRAHEDRON, 1996, 52 (02) : 531 - 550
[3] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .39. TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LYSOCELLIN .1. STEREOCONTROLLED SYNTHESIS OF THE C1-C9 AND C16-C23 FRAGMENTS
HORITA, K
INOUE, T
TANAKA, K
YONEMITSU, O
TETRAHEDRON LETTERS, 1992, 33 (38) : 5537 - 5540
[4] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .23. HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN .1. SYNTHESIS OF THE LEFT (C1-C9) AND MIDDLE (C10-C17) SEGMENTS FROM D-GLUCOSE
HORITA, K
OIKAWA, Y
YONEMITSU, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (07) : 1698 - 1704
[5] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .25. HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN .3. TOTAL SYNTHESIS OF SALINOMYCIN VIA COUPLING OF C1-C9, C10-C17, AND C18-C30 SEGMENTS
HORITA, K
OIKAWA, Y
NAGATO, S
YONEMITSU, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (07) : 1717 - 1725
[6] STUDIES DIRECTED TOWARD THE SYNTHESIS OF LYSOCELLIN CLASS POLYETHER ANTIBIOTICS - THE ASYMMETRIC-SYNTHESIS OF THE C1-C9 FERENSIMYCIN SYNTHON
EVANS, DA
POLNIASZEK, RP
TETRAHEDRON LETTERS, 1986, 27 (47) : 5683 - 5686
[7] Total synthesis of milbemycin G: Synthesis of the C(1)-C(10) fragment
Bailey, S
Teerawutgulrag, A
Thomas, EJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) : 2519 - 2520
[8] A CHEMOENZYMATIC SYNTHESIS OF THE C1-C9 FRAGMENT OF BRYOSTATIN - UNUSUAL DIASTEREOSELECTIVITY DURING A MUKAIYAMA ALDOL CONDENSATION
ROY, R
REY, AW
SYNLETT, 1990, (08) : 448 - 450
[9] Studies towards the total synthesis of Tedanolide: Synthesis of C(1)-C(9) fragment
Nyavanandi, Vijay Kumar
Nanduri, Srinivas
Andra, Naidu
Iqbal, Javed
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[10] A total synthesis of milbemycin G: approaches to the C(1)-C(10)-fragment and completion of the synthesis
Bailey, S
Helliwell, M
Teerawutgulrag, A
Thomas, EJ
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (20) : 3654 - 3677

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