Total synthesis of dolatrienoic acid: A subunit of dolastatin 14

被引：29

作者：

Moune, S ^{[1
]}

Niel, G ^{[1
]}

Busquet, M ^{[1
]}

Eggleston, I ^{[1
]}

Jouin, P ^{[1
]}

机构：

[1] UPR 9023,F-34094 MONTPELLIER 5,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo962217a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

引用

页码：3332 / 3339

页数：8

共 25 条

[1] ALLERGENIC ALPHA-METHYLENE-GAMMA-BUTYROLACTONES - STEREOSPECIFIC SYNTHESES OF (+)- AND (-)-GAMMA-METHYL-ALPHA-METHYLENE-GAMMA-BUTYROLACTONES - A STUDY OF THE SPECIFICITY OF (+) AND (-) ENANTIOMERS IN INDUCING ALLERGIC CONTACT-DERMATITIS
BARBIER, P
BENEZRA, C
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (08) : 943 - 946
[2] CHAUDHARY SK, 1979, TETRAHEDRON LETT, V2, P99
[3] JASPLAKINOLIDE, A CYCLODEPSIPEPTIDE FROM THE MARINE SPONGE, JASPIS SP
CREWS, P
MANES, LV
BOEHLER, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (25) : 2797 - 2800
[4] FLEMING I, 1985, TETRAHEDRON LETT, V26, P397
[5] HARADA T, 1994, SYNLETT, P95
[6] STEREOSELECTIVE ACETALIZATION OF 1,3-ALKANEDIOLS BY 1-MENTHONE - APPLICATION TO THE RESOLUTION OF RACEMIC 1,3-ALKANEDIOLS AND TO THE DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ENANTIOMERIC 1,3-ALKANEDIOLS
HARADA, T
KUROKAWA, H
KAGAMIHARA, Y
TANAKA, S
INOUE, A
OKU, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1412 - 1421
[7] HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, pCH2
[8] ANION-CATALYZED REACTIONS OF SILYL ESTER POLYENOLATES WITH ELECTROPHILES
HERTLER, WR
REDDY, GS
SOGAH, DY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3532 - 3539
[9] HUET F, 1978, SYNTHETIC COMMUN, V8, P63
[10] ISOLATION AND STEREOSTRUCTURE OF DOLICULIDE, A CYTOTOXIC CYCLODEPSIPEPTIDE FROM THE JAPANESE SEA HARE DOLABELLA-AURICULARIA
ISHIWATA, H
NEMOTO, T
OJIKA, M
YAMADA, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) : 4710 - 4711

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