Total synthesis of zoanthamine alkaloids .2. Construction of the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of zoanthamine

被引：26

作者：

Tanner, D

Tedenborg, L

Somfai, P

机构：

[1] UNIV UPPSALA, DEPT ORGAN CHEM, S-75121 UPPSALA, SWEDEN

[2] LUND UNIV, CTR CHEM, LUND INST TECHNOL, S-22100 LUND, SWEDEN

来源：

ACTA CHEMICA SCANDINAVICA | 1997年 / 51卷 / 12期

关键词：

D O I：

10.3891/acta.chem.scand.51-1217

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

This paper describes the construction of three key intermediates 11, 15 and 23 for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of the target molecule, are synthesised efficiently from (R)-gamma-hydroxymethyl-gamma-butyrolactone, methyl propiolate, and (S)-perillyl alcohol, respectively.

引用

页码：1217 / 1223

页数：7

共 15 条

[1] CHAUDHARY SK, 1979, TETRAHEDRON LETT, P99
[2] 2 UNPRECEDENTED OBSERVATIONS IN ORGANOCUPRATE CHEMISTRY - REVERSIBILITY OF ADDITION TO AN ALKYNE AND LOW PKA OF A STANNYLCUPRATE
COX, SD
WUDL, F
[J]. ORGANOMETALLICS, 1983, 2 (01) : 184 - 185
[3] LANTHANIDE CATALYSIS OF CYCLO-ADDITIONS OF HETERODIENES WITH ENOL ETHERS
DANISHEFSKY, S
BEDNARSKI, M
[J]. TETRAHEDRON LETTERS, 1984, 25 (07) : 721 - 724
[4] STEREOCHEMICAL CONTROL OF NATURES BIOSYNTHETIC PATHWAYS - A GENERAL STRATEGY FOR THE SYNTHESIS OF POLYPROPIONATE-DERIVED STRUCTURAL UNITS FROM A SINGLE CHIRAL PROGENITOR
HANESSIAN, S
MURRAY, PJ
[J]. TETRAHEDRON, 1987, 43 (21) : 5055 - 5072
[5] SYNTHETIC STUDIES ON THE MEVINIC ACIDS USING THE CHIRON APPROACH - TOTAL SYNTHESIS OF (+)-DIHYDROMEVINOLIN
HANESSIAN, S
ROY, PJ
PETRINI, M
HODGES, PJ
DIFABIO, R
CARGANICO, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) : 5766 - 5777
[6] LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[7] TRIMETHYLSTANNYLVINYL CUPRATES GENERATION AND 1,4-CONJUGATE ADDITION TO ALPHA,BETA-UNSATURATED-KETONES
PEREIRA, OZ
CHAN, TH
[J]. TETRAHEDRON LETTERS, 1995, 36 (48) : 8749 - 8752
[8] STEREOSELECTIVE CONJUGATE ADDITION OF LITHIUM (PHENYLTHIO)(TRIMETHYLSTANNYL) CUPRATE TO ALPHA,BETA-ACETYLENIC ESTERS - PREPARATION OF (E)-4-LITHIO-1,3-PENTADIENES AND (Z)-4-LITHIO-1,3-PENTADIENES AND THEIR REACTION WITH ELECTROPHILES
PIERS, E
MORTON, HE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4263 - 4264
[9] REACTION OF (TRIMETHYLSTANNYL)COPPER REAGENTS WITH ALPHA,BETA-ACETYLENIC ESTERS
PIERS, E
CHONG, JM
MORTON, HE
[J]. TETRAHEDRON LETTERS, 1981, 22 (49) : 4905 - 4908
[10] ZOANTHAMINE - A NOVEL ALKALOID FROM A MARINE ZOANTHID
RAO, CB
ANJANEYULA, ASR
SARMA, NS
VENKATATESWARLU, Y
ROSSER, RM
FAULKNER, DJ
CHEN, MHM
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) : 7983 - 7984

← 1 2 →