A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction

被引：33

作者：

Barluenga, J ^{[1
]}

Mateos, C ^{[1
]}

Aznar, F ^{[1
]}

Valdés, C ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, CSIC, Oviedo 33071, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 11期

关键词：

D O I：

10.1021/ol0260021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A short and convergent synthesis of 5,8-disubstituted indolizidine and 1,4-quinolizidine scaffolds is described. The key steps of the synthetic pathway are the aza-Diels-Alder reaction of a 2-aminodiene with an N-allyl or N-homoallylaldimine and a ring-closing metathesis. The bicyclic alkaloid analogues are obtained with total diastereoselectivity and through a common pathway.

引用

页码：1971 / 1974

页数：4

共 34 条

[21] A formal synthesis of castanospermine using an olefin metathesis cyclisation reaction as a key step
Overkleeft, HS
Pandit, UK
[J]. TETRAHEDRON LETTERS, 1996, 37 (04) : 547 - 550
[22] SYNTHESIS OF (-)-SLAFRAMINE AND RELATED INDOLIZIDINES
PEARSON, WH
BERGMEIER, SC
WILLIAMS, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3977 - 3987
[23] Synthesis of (-)-lasubine(I) via a planar chiral [(η6-arene)Cr(CO)3] complex
Ratni, H
Kundig, EP
[J]. ORGANIC LETTERS, 1999, 1 (12) : 1997 - 1999
[24] Carbon-carbon bond-forming solid-phase reactions. Part II
Sammelson, RE
Kurth, MJ
[J]. CHEMICAL REVIEWS, 2001, 101 (01) : 137 - 202
[25] Synthesis and applications of RuCl2(=CHR')(PR(3))(2): The influence of the alkylidene moiety on metathesis activity
Schwab, P
Grubbs, RH
Ziller, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) : 100 - 110
[26] Seneci P., 2000, SOLID PHASE SYNTHESI
[27] TIETZE LF, 1997, TOP CURR CHEM, P190
[28] WALDMANN H, 1995, SYNLETT, P133
[29] Waldmann H., 1994, SYNTHESIS, P535
[30] ALKALOID TOTAL SYNTHESIS BY INTRAMOLECULAR IMINO DIELS-ALDER CYCLO-ADDITIONS
WEINREB, SM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (01) : 16 - 21

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