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 50 条

[41] Studies on the stereochemistry of amphidinolides: Synthesis of a diastereomer of the C-1-C-9 fragment of amphidinolide C
Ishiyama, H
Ishibashi, M
Kobayashi, J
CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (10) : 1819 - 1822
[42] Toward a Total Synthesis of Divergolide A; Synthesis of the Amido Hydroquinone Core and the C10-C15 Fragment
Zhao, Guanglian
Wu, Jinlong
Dai, Wei-Min
SYNLETT, 2012, (19) : 2845 - 2849
[43] Studies directed toward the total synthesis of discodermolide: Asymmetric synthesis of the C1-C14 fragment
Arefolov, A
Panek, JS
ORGANIC LETTERS, 2002, 4 (14) : 2397 - 2400
[44] Progress toward the Total Synthesis of Goniodomin A: Stereocontrolled, Convergent Synthesis of the C12-C36 Fragment
Fuwa, Haruhiko
Matsukida, Seiji
Miyoshi, Taro
Kawashima, Yuki
Saito, Tomoyuki
Sasaki, Makoto
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06): : 2213 - 2227
[45] A Formal Synthesis of the C1-C9 Fragment of Amphidinolide C Employing the Tamaru Reaction
Paudyal, Mahesh P.
Rath, Nigam P.
Spilling, Christopher D.
ORGANIC LETTERS, 2010, 12 (13) : 2954 - 2957
[46] A Carbohydrate-Based Synthesis of the C13-C22 Fragment of Amphidinolide X
Gurjar, Mukund K.
Yellol, Gorakh S.
Mohapatra, Debendra K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (09) : 1753 - 1758
[47] Toward the Total Synthesis of Vinigrol: Synthesis of epi-C-8-Dihydrovinigrol
Gentric, Lionel
Le Goff, Xavier
Ricard, Louis
Hanna, Issam
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24): : 9337 - 9344
[48] Progress toward the total synthesis of spongistatin 1 (altohyrtin A): Completion of the C29-C43 fragment (EF pyran rings).
Katz, JD
Crimmins, MT
Washburn, DG
McAtee, LF
Kirincich, SJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U53 - U53
[49] Toward the total synthesis of Antascomicin B: Building the C10-C21 fragment
Rivero-Castro, Juliette
McIntosh, Matthias C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[50] Synthetic studies toward the total synthesis of amphidinolide B
Carter, RG
Zhang, W
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U170 - U170

← 1 2 3 4 5 →