Asymmetric Total Synthesis of (+)-Fusarisetin A via the Intramolecular Pauson-Khand Reaction

被引：42

作者：

Huang, Jun ^{[1
]}

Fang, Lichao ^{[1
]}

Long, Rong ^{[1
]}

Shi, Li-Li ^{[1
]}

Shen, Hong-Juan ^{[1
]}

Li, Chuang-chuang ^{[1
]}

Yang, Zhen ^{[1
,2
,3
,4
]}

机构：

[1] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[3] Peking Univ, BNLMS, Beijing 100871, Peoples R China

[4] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

基金：

美国国家科学基金会;

关键词：

ABSOLUTE-CONFIGURATION; N-OXIDE; ACID; CONSTRUCTION; DERIVATIVES; (-)-FUSARISETIN; FUSARISETIN; OXIRANES; KETONES; FUNGUS;

D O I：

10.1021/ol401831w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetic total synthesis of (+)-fusarisetin A has been achieved. The essential to our strategy was the application of the intramolecular Pauson-Khand reaction for the stereoselective construction of the trans-decalin subunit of (+)-fusarisetin A with a unique C16 quarternary chiral center. The developed chemistry offers an alternative to the IMDA reaction that has been used for fusarisetin A, and is applicable to analogue synthesis for biological evaluation.

引用

页码：4018 / 4021

页数：4

共 50 条

[41] The tandem Pauson-Khand reaction
Thommen, M
Veretenov, AL
GuidettiGrept, R
Keese, R
HELVETICA CHIMICA ACTA, 1996, 79 (02) : 461 - 476
[42] THE DIRECTED PAUSON-KHAND REACTION
KRAFFT, ME
JULIANO, CA
SCOTT, IL
WRIGHT, C
MCEACHIN, MD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) : 1693 - 1703
[43] Interrupted Pauson-Khand reaction
Krafft, M.E.
Wilson, A.M.
Dasse, O.A.
Shao, B.
Cheung, Y.Y.
Fu, Z.
Bonaga, L.V.R.
Mollman, M.K.
Journal of the American Chemical Society, 1996, 118 (25):
[44] Seven membered rings via intramolecular Pauson-Khand reactions
Pérez-Serrano, L
Casarrubios, L
Domínguez, G
Pérez-Castells, J
CHEMICAL COMMUNICATIONS, 2001, (24) : 2602 - 2603
[45] Heterobimetallic alkyne complexes in organic synthesis: An asymmetric variant of the Pauson-Khand reaction
Rutherford, DT
Christie, SDR
TETRAHEDRON LETTERS, 1998, 39 (52) : 9805 - 9808
[46] STUDIES ON THE PAUSON-KHAND REACTION - SUBSTITUTION EFFECTS ON INTRAMOLECULAR CYCLIZATIONS
MONTANA, AM
MOYANO, A
PERICAS, MA
SERRATOSA, F
ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1988, 84 (01): : 82 - 88
[47] Synthesis of highly functionalized pentalenes via intermolecular Pauson-Khand reaction
Becheanu, Armand
Baro, Angelika
Laschat, Sabine
Frey, Wolfgang
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) : 2215 - 2225
[48] Concise Synthesis of 11-Noriridoids via Pauson-Khand Reaction
Kouda, Ryuji
Yamamoto, Kazuki
Katsuyama, Akira
Ichikawa, Satoshi
Yakushiji, Fumika
CHEMICAL & PHARMACEUTICAL BULLETIN, 2024, 72 (06) : 547 - 558
[49] Asymmetric catalytic intramolecular Pauson-Khand reactions with Ir(phox) catalysts
Lu, Zhong-Lin
Neumann, Eva
Pfaltz, Andreas
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (25) : 4189 - 4192
[50] Identification of an asymmetric Pauson-Khand precatalyst
Gibson, SE
Lewis, SE
Loch, JA
Steed, JW
Tozer, MJ
ORGANOMETALLICS, 2003, 22 (26) : 5382 - 5384

← 1 2 3 4 5 →