SYNTHESIS OF TRANS-14-PHENYLSULFONYL-1,7,9-TRIOXADISPIRO[5.1.5.3]HEXADECANE AND CIS-14-PHENYLSULFONYL-1,7,9-TRIOXADISPIRO[5.1.5.3]HEXADECANE

被引：16

作者：

BRIMBLE, MA ^{[1
]}

RUSH, CJ ^{[1
]}

机构：

[1] MASSEY UNIV,DEPT CHEM & BIOCHEM,PALMERSTON NORTH,NEW ZEALAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 05期

关键词：

D O I：

10.1039/p19940000497

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the trans- and cis-isomers 1a and 1b of 14-phenylsulfonyl-1,7,9-trioxadispiro-[5.1.5.3]hexadecane via the addition of an alpha-sulfonyl carbanion to delta-valerolactone followed by acid-catalysed cyclization is described. Reductive removal of the sulfone group using Raney nickel afforded the parent bis-spiroacetals 9a and 9b together with the spiroacetal alcohol 10 which underwent oxidative cyclization to the parent bis-spiroacetals 9a and 9b upon treatment with iodobenzene diacetate and iodine.

引用

页码：497 / 500

页数：4

共 14 条

[1] STRUCTURE OF A BIS-SPIROACETAL, CIS-14-PHENYLSULFONYL-1,7,9-TRIOXADISPIRO[5.1.5.3]-HEXADECANE
BAKER, EN
BRIMBLE, MA
NORRIS, GE
QUAIL, JW
RUSH, CA
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 1857 - 1859
[2] SULFIDE GROUP AS AN ALDEHYDE PRECURSOR
BAKUZIS, P
BAKUZIS, MLF
FORTES, CC
SANTOS, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (16) : 2769 - 2770
[3] 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
[4] A FACILE SYNTHESIS OF SPIROKETALS
BRIMBLE, MA
OFFICER, DL
WILLIAMS, GM
[J]. TETRAHEDRON LETTERS, 1988, 29 (29) : 3609 - 3612
[5] THE CHEMISTRY OF BIS-SPIROACETALS - SYNTHESIS OF THE NOVEL 1,7,9-TRIOXADISPIRO[5.1.5.3]HEXADECANE RING-SYSTEM
BRIMBLE, MA
RUSH, CJ
WILLIAMS, GM
BAKER, EN
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02): : 414 - 416
[6] BRIMBLE MA, 1992, J ORG CHEM, V52, P5818
[7] 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
[8] COTTIER L, 1981, TETRAHEDRON, V37, P2525
[9] 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
[10] Kishi Y., 1982, FRONT CHEM, P287

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