Synthesis of the C1-C13 fragment of leucascandrolide A

被引：38

作者：

Crimmins, MT ^{[1
]}

Carroll, CA ^{[1
]}

King, BW ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 05期

关键词：

D O I：

10.1021/ol991345t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis of the C1-C13 fragment 3 of leucascandrolide A has been completed utilizing a stereoselective and regioselective reductive cleavage of a highly functionalized spiroketal to incorporate the cis-2,6-disubstituted tetrahydropyan. The spiroketal was constructed by addition of a lithiated, pyrone 5 to aldehyde 6.

引用

页码：597 / 599

页数：3

共 14 条

[1] AMBROSIO MD, 1996, HELV CHIM ACTA, V79, P51
[2] A method for constructing the C2-C12 dispiroacetal moiety of altohyrtin A
Claffey, MM
Heathcock, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) : 7646 - 7647
[3] Regioselective and stereoselective reductive cleavage of 1,7-dioxaspiro[5.5]undecane alcohols
Crimmins, MT
Rafferty, SW
[J]. TETRAHEDRON LETTERS, 1996, 37 (32) : 5649 - 5652
[4] Synthesis of the AB spiroketal subunit of spongistatin 1 (altohyrtin A): The pyrone approach
Crimmins, MT
Washburn, DG
[J]. TETRAHEDRON LETTERS, 1998, 39 (41) : 7487 - 7490
[5] Asymmetric total synthesis of (+)-milbemycin D
Crimmins, MT
Alawar, RS
Vallin, IM
Hollis, WG
OMahony, R
Lever, JG
BankaitisDavis, DM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) : 7513 - 7528
[6] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN
EVANS, DA
DOW, RL
SHIH, TL
TAKACS, JM
ZAHLER, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) : 5290 - 5313
[7] NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES
EVANS, DA
URPI, F
SOMERS, TC
CLARK, JS
BILODEAU, MT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) : 8215 - 8216
[8] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN
EVANS, DA
KALDOR, SW
JONES, TK
CLARDY, J
STOUT, TJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) : 7001 - 7031
[9] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS
HORITA, K
YOSHIOKA, T
TANAKA, T
OIKAWA, Y
YONEMITSU, O
[J]. TETRAHEDRON, 1986, 42 (11) : 3021 - 3028
[10] ACYCLIC STEREOSELECTION .20. HIGH DIASTEREOFACIAL SELECTIVITY IN THE STANNIC CHLORIDE MEDIATED REACTIONS OF ALLYLSILANES WITH CHIRAL ALPHA-ALKOXY AND BETA-ALKOXY ALDEHYDES
KIYOOKA, S
HEATHCOCK, CH
[J]. TETRAHEDRON LETTERS, 1983, 24 (44) : 4765 - 4768

← 1 2 →