ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF THE SIPHONARINS AND BACONIPYRONES - ENANTIOCONTROLLED SYNTHESIS OF A GAMMA-PYRONE SUBUNIT

被引：27

作者：

PATERSON, I

FRANKLIN, AS

机构：

[1] University Chemical Laboratory, Cambridge, CB2 1EW, Lensfield Road

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 37期

关键词：

D O I：

10.1016/0040-4039(94)85043-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldehyde 11 was prepared with >90% ds using a Sn(II)-mediated aldol reaction between (S)-13 and (S)-14. Conversion into the gamma-pyrone 8, a known degradation product from dihydrosiphonarin B, established the absolute configuration as enantiomeric to that shown in 4.

引用

页码：6925 / 6928

页数：4

共 24 条

[1] CHEMICAL-PROPERTIES OF BETA-TRIKETONES - REEXAMINATION OF ALBIZATIS TANDEM ALDOL PROCESS
ARIMOTO, H
OHBA, S
NISHIYAMA, S
YAMAMURA, S
[J]. TETRAHEDRON LETTERS, 1994, 35 (26) : 4581 - 4584
[2] MILD CONDITIONS FOR CYCLIZATION OF BETA-TRIKETIDES TO THE CORRESPONDING GAMMA-PYRONES CARRYING ADJACENT CHIRAL CENTERS TOWARD BIOMIMETIC SYNTHESIS OF FULLY SUBSTITUTED GAMMA-PYRONE-CONTAINING NATURAL-PRODUCTS
ARIMOTO, H
NISHIYAMA, S
YAMAMURA, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5619 - 5620
[3] SYNTHETIC STUDIES ON FULLY SUBSTITUTED GAMMA-PYRONE-CONTAINING NATURAL-PRODUCTS - SYNTHESIS OF GAMMA-PYRONE DERIVATIVES OBTAINED BY DECOMPOSITION OF PERONIATRIOLS
ARIMOTO, H
NISHIYAMA, S
YAMAMURA, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (38) : 5491 - 5494
[4] SYNTHETIC STUDIES ON FULLY SUBSTITUTED GAMMA-PYRONE-CONTAINING NATURAL-PRODUCTS - THE ABSOLUTE-CONFIGURATIONS OF ILIKONAPYRONE AND PERONIATRIOL-I AND PERONIATRIOL-II
ARIMOTO, H
CHENG, JF
NISHIYAMA, S
YAMAMURA, S
[J]. TETRAHEDRON LETTERS, 1993, 34 (36) : 5781 - 5784
[5] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
[6] DIASTEREOSELECTIVE ALDOL REACTIONS USING BETA-KETO IMIDE DERIVED ENOLATES - A VERSATILE APPROACH TO THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS
EVANS, DA
CLARK, JS
METTERNICH, R
NOVACK, VJ
SHEPPARD, GS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 866 - 868
[7] SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS
EVANS, DA
HOVEYDA, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6447 - 6449
[8] STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS
EVANS, DA
RIEGER, DL
BILODEAU, MT
URPI, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 1047 - 1049
[9] A CONFIGURATIONAL MODEL FOR SIPHONARIID POLYPROPIONATES DERIVED FROM STRUCTURAL AND BIOSYNTHETIC CONSIDERATIONS
GARSON, MJ
GOODMAN, JM
PATERSON, I
[J]. TETRAHEDRON LETTERS, 1994, 35 (37) : 6929 - 6932
[10] BIOSYNTHETIC-STUDIES ON POLYPROPIONATES - A STEREOCHEMICAL MODEL FOR SIPHONARIN-A AND SIPHONARIN-B FROM THE PULMONATE LIMPET SIPHONARIA ZELANDICA
GARSON, MJ
JONES, DD
SMALL, CJ
LIANG, J
CLARDY, J
[J]. TETRAHEDRON LETTERS, 1994, 35 (37) : 6921 - 6924

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