Towards the synthesis of Palmerolide A: asymmetric synthesis of C1-C14 fragment

被引：27

作者：

Chandrasekhar, S. ^{[1
]}

Vijeender, K. ^{[1
]}

Chandrashekar, G. ^{[1
]}

Reddy, Ch. Raji ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2007.10.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of a C1-C14 fragment of a marine cytotoxic natural product Palmerolide A is described. The key steps involved in this synthesis are deoxygenative rearrangement of an alkynol followed by an asymmetric dihydroxylation of a diene ester and CBS-reduction. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2473 / 2478

页数：6

共 20 条

[1] Concise synthesis of truncated pachastrissamine (jaspine B) and its enantiomer [J].

Chandrasekhar, S. ;

Tiwari, Bhoopendra ;

Prakash, S. Jaya .

ARKIVOC, 2006, :155-161

[2] Stereoselective synthesis of the C1-C20 segment of the microsclerodermins A and B [J].

Chandrasekhar, S. ;

Sultana, S. Shameem .

TETRAHEDRON LETTERS, 2006, 47 (40) :7255-7258

[3] Synthesis of functionalized C ring equivalent of Eleutherobin [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Jagadeshwar, V ;

Sultana, SS .

ARKIVOC, 2005, :92-98

[4] The first stereoselective total synthesis of (6,S)-5,6-dihydro-1(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, MS .

TETRAHEDRON LETTERS, 2004, 45 (50) :9299-9301

[5] Design, synthesis and cytotoxic studies on the simplified oxy analog of eleutherobin [J].

Chandrasekhar, S ;

Jagadeshwar, V ;

Narsihmulu, C ;

Sarangapani, M ;

Krishna, DR ;

Vidyasagar, J ;

Vijay, D ;

Sastry, GN .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3687-3689

[6] Towards a synthesis of epothilone A: asymmetric synthesis of C(1)-C(6) and C(7)-(15) fragments [J].

Chandrasekhar, S ;

Reddy, CR .

TETRAHEDRON-ASYMMETRY, 2002, 13 (03) :261-268

[7]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[8]

2-Z

[9] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[10] Palmerolide A, a cytotoxic macrolide from the Antarctic tunicate Synoicum adareanum [J].

Diyabalanage, T ;

Amsler, CD ;

McClintock, JB ;

Baker, BJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5630-5631

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