Synthesis of highly substituted tetrahydropyrans: preparation of the C20-C28 moiety of phorboxazoles

被引：23

作者：

Chakraborty, TK ^{[1
]}

Reddy, VR ^{[1
]}

Reddy, TJ ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Bioorgan Lab, Organ Div 3, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 43期

关键词：

epoxy alcohols; Sharpless epoxidation; epoxide opening; 2-methyl-1,3-diol; phorboxazoles;

D O I：

10.1016/j.tet.2003.08.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A propionate-derived polyketide building block A whose 2-methyl-1,3-diol moiety was built by a Ti(III)-mediated ring opening reaction of a trisubstituted 2,3-epoxy alcohol precursor was employed as a common starting material for the syntheses of highly substituted tetrahydropyrans 1-5, the first one being the C20-C28 fragment of cytotoxic natural products, phorboxazoles. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8613 / 8622

页数：10

共 52 条

[1] Stereocontrolled synthesis of 2,4,5-trisubstituted tetrahydropyrans [J].

Al-Mutairi, EH ;

Crosby, SR ;

Darzi, J ;

Harding, JR ;

Hughes, RA ;

King, CD ;

Simpson, TJ ;

Smith, RW ;

Willis, CL .

CHEMICAL COMMUNICATIONS, 2001, (09) :835-836

[2] Annonaceous acetogenins: Recent progress [J].

Alali, FQ ;

Liu, XX ;

McLaughlin, JL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :504-540

[3]

ANH NT, 1977, NOUV J CHIM, V1, P61

[4]

[Anonymous], 1994, Org. React

[5] Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides.: Straightforward synthesis and absolute stereochemistry of (+)-3α-hydroxyreynosin and related eudesmanolides [J].

Barrero, AF ;

Oltra, JE ;

Cuerva, JM ;

Rosales, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2566-2571

[6] A new strategy for the synthesis of cyclic terpenoids based on the radical opening of acyclic epoxypolyenes [J].

Barrero, AF ;

Cuerva, JM ;

Herrador, MM ;

Valdivia, MV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :4074-4078

[7] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[8] Synthesis of chiral 1,3-diols by radical-mediated regioselective opening of 2,3-epoxy alcohols using cp2TiCl [J].

Chakraborty, TK ;

Das, S .

TETRAHEDRON LETTERS, 2002, 43 (12) :2313-2315

[9] Total synthesis of (+)-crocacin C [J].

Chakraborty, TK ;

Jayaprakash, S ;

Laxman, P .

TETRAHEDRON, 2001, 57 (46) :9461-9467

[10] Anti-Markovnikov opening of trisubstituted epoxy alcohols: application in the synthesis of 2-methyl-1,3-diols [J].

Chakraborty, TK ;

Dutta, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1257-1259

← 1 2 3 4 5 6 →