Enantioselective total synthesis of (+)-leucascandrolide A macrolactone

被引：61

作者：

Crimmins, MT ^{[1
]}

Siliphalvanh, P ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 24期

关键词：

D O I：

10.1021/ol035797o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of the (+)-leucascandrolide A macrolactone has been achieved in 20 linear steps from 1,3-propanediol. The key steps in the synthesis are a reductive cleavage of bicyclic ketal 5 to establish the C15 stereogenic center and a diastereoselective aldol of the boron enolate of methyl ketone 3 to aldehyde 4 in preparation for a heteroconjugate addition for the introduction of the C3 stereocenter.

引用

页码：4641 / 4644

页数：4

共 37 条

[21] Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A [J].

Gonzalez, A ;

Aiguade, J ;

Urpi, F ;

Vilarrasa, J .

TETRAHEDRON LETTERS, 1996, 37 (49) :8949-8952

[22] Total synthesis of leucascandrolide A [J].

Hornberger, KR ;

Hamblett, CL ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12894-12895

[23] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[24] STEREOSELECTIVE REDUCTION OF ACETALS - A METHOD FOR REDUCTIVE GENERATION OF HETEROCYCLIC RING-SYSTEMS [J].

ISHIHARA, K ;

MORI, A ;

YAMAMOTO, H .

TETRAHEDRON, 1990, 46 (13-14) :4595-4612

[25] Mukaiyama Aldol-Prins cyclization cascade reaction: A formal total synthesis of leucascandrolide A [J].

Kopecky, DJ ;

Rychnovsky, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8420-8421

[26]

KOTSUKI H, 1992, SYNLETT, P97

[27] Efficient stereochemical relay en route to leucascandrolide A [J].

Kozmin, SA .

ORGANIC LETTERS, 2001, 3 (05) :755-758

[28] OSMIUM TETROXIDE-CATALYZED PERIODATE OXIDATION OF OLEFINIC BONDS [J].

PAPPO, R ;

ALLEN, DS ;

LEMIEUX, RU ;

JOHNSON, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :478-479

[29] A fully stereocontrolled total synthesis of (+)-leucascandrolide A [J].

Paterson, I ;

Tudge, M .

TETRAHEDRON, 2003, 59 (35) :6833-6849

[30] Stereocontrolled total synthesis of (+)-leucascandrolide A [J].

Paterson, I ;

Tudge, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (03) :343-+

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