Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment

被引：11

作者：

Kawashima, Yuki ^{[1
]}

Toyoshima, Atsushi ^{[1
]}

Fuwa, Haruhiko ^{[1
]}

Sasaki, Makoto ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Life Sci, Aoba Ku, 2-1-1 Katahira, Sendai, Miyagi 9808577, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

基金：

日本学术振兴会;

关键词：

CARIBENOLIDE-I STRUCTURES; SECONDARY ALCOHOLS; OLEFIN METATHESIS; ANTITUMOR MACROLIDE; SELECTIVE OXIDATION; PROPOSED STRUCTURE; DIRECT CONVERSION; ENOL ETHERS; RING; STRATEGY;

D O I：

10.1021/acs.orglett.6b00871

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the C8-C29 fragment of amphidinolide N, a potent cytotoxic macrolide isolated from the marine dinoflagellate Amphidinium sp., has been achieved. The key features of the synthesis involve a convergent union of the C9-C15 and C16-C29 fragments by Steglich esterification and the construction of a pyran unit through a Tebbe methylenation/ring-closing metathesis sequence.

引用

页码：2232 / 2235

页数：4

共 58 条

[1] ANELLI PL, 1987, J ORG CHEM, V52, P2559
[2] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES
BAL, BS
CHILDERS, WE
PINNICK, HW
[J]. TETRAHEDRON, 1981, 37 (11) : 2091 - 2096
[3] Applications of CeCl3 as an Environmental Friendly Promoter in Organic Chemistry
Bartoli, Giuseppe
Marcantoni, Enrico
Marcolini, Mauro
Sambri, Letizia
[J]. CHEMICAL REVIEWS, 2010, 110 (10) : 6104 - 6143
[4] ISOLATION AND STRUCTURE OF CARIBENOLIDE-I, A HIGHLY POTENT ANTITUMOR MACROLIDE FROM A CULTURED FREE-SWIMMING CARIBBEAN DINOFLAGELLATE, AMPHIDINIUM SP S1-36-5
BAUER, I
MARANDA, L
YOUNG, KA
SHIMIZU, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) : 1084 - 1086
[5] HYDROBORATION .61. DIISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY - IMPROVED PREPARATION AND ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS-DISUBSTITUTED ALKENES
BROWN, HC
DESAI, MC
JADHAV, PK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) : 5065 - 5069
[6] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
[7] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
[8] The dihydroxyacetone unit -: A versatile C3 building block in organic synthesis
Enders, D
Voith, M
Lenzen, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) : 1304 - 1325
[9] Total synthesis of bryostatin 2
Evans, DA
Carter, PH
Carreira, EM
Charette, AB
Prunet, JA
Lautens, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7540 - 7552
[10] THE SILYLCUPRATION OF ACETYLENES - A SYNTHESIS OF VINYLSILANES
FLEMING, I
NEWTON, TW
ROESSLER, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2527 - 2532

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