Synthesis of (5R,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane

被引：15

作者：

Dorta, RL

Martin, A

Suarez, E

Prange, T

机构：

[1] CSIC,INST PROD NAT & AGROBIOL,LA LAGUNA 38206,TENERIFE,SPAIN

[2] UNIV PARIS 11,LURE,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 07期

关键词：

D O I：

10.1016/0957-4166(96)00227-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of (5R, 7S, 13S)- and (5S, 7S, 13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3] pentadecane from tri-O-acetyl-D-glucal, by a convenient homologation of C-l and C-6 atoms which led to an appropriate dihydroxyl intermediate 7, is reported. The key steps for the construction of the two spiroacetal systems involved a double, step by step, radical abstraction promoted by (diacetoxyiodo)benzene and iodine. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1907 / 1910

页数：4

共 17 条

[1] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS
BOIVIN, TLB
[J]. TETRAHEDRON, 1987, 43 (15) : 3309 - 3362
[2] CHEMISTRY OF BIS-SPIROACETALS - SYNTHESIS OF CIS-1-(2-METHYL-1,6,8-TRIOXADISPIRO[4.1.5.3]PENTADEC-13-EN-2-YL)METHANOL AND TRANS-1-(2-METHYL-1,6,8-TRIOXADISPIRO[4.1.5.3]PENTADEC-13-EN-2-YL)METHANOL
BRIMBLE, MA
WILLIAMS, GM
BAKER, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09): : 2221 - 2227
[3] SYNTHESIS OF THE BIS-SPIROACETAL MOIETY OF 17-EPI-20-DEOXYSALINOMYCIN
BRIMBLE, MA
WILLIAMS, GM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5818 - 5822
[4] STEREOSELECTIVE SYNTHESES OF KINETIC AND THERMODYNAMIC ISOMERS OF ALKOXY-SPIROKETALS AND OF TRIOXA-BIS-SPIROKETALS
COTTIER, L
DESCOTES, G
[J]. TETRAHEDRON, 1985, 41 (02) : 409 - 412
[5] ON THE ADDITION OF ALLYLTRIMETHYLSILANE TO GLYCAL ACETATES
DANISHEFSKY, S
KERWIN, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) : 3803 - 3805
[6] CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .22. A HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN - CRUCIAL ROLE OF THE 4-METHOXYBENZYL (MPM) PROTECTING GROUP FOR HYDROXY FUNCTIONS
HORITA, K
OIKAWA, Y
NAGATO, S
YONEMITSU, O
[J]. TETRAHEDRON LETTERS, 1988, 29 (40) : 5143 - 5146
[7] STEREOSELECTIVE SYNTHESIS OF THE MIDDLE (C10-C17) AND RIGHT (C18-C30) SEGMENTS, AND THEIR COUPLING TO COMPLETE A FORMAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC SALINOMYCIN
HORITA, K
NAGATO, S
OIKAWA, Y
YONEMITSU, O
[J]. TETRAHEDRON LETTERS, 1987, 28 (28) : 3253 - 3256
[8] KINASHI H, 1973, TETRAHEDRON LETT, P4955
[9] Kishi Y., 1982, FRONT CHEM, P287
[10] KLUGE AF, 1986, HETEROCYCLES, V24, P1699

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