Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans

被引：64

作者：

Schmidt, B ^{[1
]}

Wildemann, H ^{[1
]}

机构：

[1] Univ Dortmund, Fachbereich Chem, D-44227 Dortmund, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 18期

关键词：

D O I：

10.1021/jo005534x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from alpha-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.

引用

页码：5817 / 5822

页数：6

共 50 条

[41] Efficient synthesis of spirolactams by ring-closing olefin metathesis
Kang, SW
Kim, SH
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2006, 27 (01): : 153 - 154
[42] Efficient synthesis of enantiopure conduritols by ring-closing metathesis
Jorgensen, M
Iversen, EH
Paulsen, AL
Madsen, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13): : 4630 - 4634
[43] Synthesis of various secosteroidal macrocycles by ring-closing metathesis
Ibrahim-Ouali, Malika
Romero, Eugenie
[J]. STEROIDS, 2013, 78 (07) : 651 - 661
[44] Application of ring-closing metathesis reactions in the synthesis of epothilones
Rivkin, A
Cho, YS
Gabarda, AE
Yoshimura, F
Danishefsky, SJ
[J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (02): : 139 - 143
[45] Formal synthesis of valienamine using ring-closing metathesis
Cumpstey, I
[J]. TETRAHEDRON LETTERS, 2005, 46 (37) : 6257 - 6259
[46] Synthesis of catenane structures via ring-closing metathesis
Weck, M
Mohr, B
Sauvage, JP
Grubbs, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15): : 5463 - 5471
[47] Synthesis of conformationally restricted dinucleotides by ring-closing metathesis
Sorensen, AM
Nielsen, P
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4217 - 4219
[48] Ring-closing olefin metathesis for the synthesis of benzene derivatives
Yoshida, Kazuhiro
Kawagoe, Fumihiro
Iwadate, Noriyuki
Takahashi, Hidetoshi
Imamoto, Tsuneo
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (04) : 611 - 613
[49] Total synthesis of (-)- and (±)-frontalin via ring-closing metathesis
Scholl, M
Grubbs, RH
[J]. TETRAHEDRON LETTERS, 1999, 40 (08) : 1425 - 1428
[50] Total synthesis of (-)-nakadomarin A: alkyne ring-closing metathesis
Jakubec, Pavol
Kyle, Andrew F.
Calleja, Jonas
Dixon, Darren J.
[J]. TETRAHEDRON LETTERS, 2011, 52 (46) : 6094 - 6097

← 1 2 3 4 5 →