Enantioselective Synthesis of (+)-Isolysergol via Ring-Closing Metathesis

被引：43

作者：

Deck, Jason A. ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

基金：

美国国家卫生研究院;

关键词：

FUSED NITROGEN-HETEROCYCLES; LYSERGIC-ACID; OLEFIN-METATHESIS; ERGOT ALKALOIDS; ASYMMETRIC-SYNTHESIS; (&/-)-LYSERGIC ACID; (+/-)-LYSERGIC ACID; (+)-LYSERGIC ACID; MANZAMINE-A; CYCLIZATION;

D O I：

10.1021/ol100819f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective synthesis of (+)-isolysergol was completed in 12 steps from commercially available materials by a novel approach that features a late stage microwave-mediated, diastereomeric ring-closing metathesis catalyzed by a chiral molybdenum catalyst to simultaneously form the D ring and set the stereocenter at C(8).

引用

页码：2610 / 2613

页数：4

共 50 条

[1] Enantioselective synthesis of (+)-isolysergol via ring closing metathesis
Deck, Jason A.
Martin, Stephen F.
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[2] Synthesis of cyclitols via ring-closing metathesis
Kornienko, A
d'Alarcao, M
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (05) : 827 - 829
[3] Synthesis of "glycospirostanes" via ring-closing metathesis
Czajkowska, Dorota
Morzycki, Jacek W.
Santillan, Rosa
Siergiejczyk, Leszek
[J]. STEROIDS, 2009, 74 (13-14) : 1073 - 1079
[4] Template Synthesis for Disilamacrocycles via Ring-closing Metathesis
Tu, Yuyang
Inagaki, Yusuke
Kwon, Eunsang
Setaka, Wataru
[J]. CHEMISTRY LETTERS, 2021, 50 (07) : 1397 - 1399
[5] 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
[6] Total synthesis of (-)- and (±)-frontalin via ring-closing metathesis
Scholl, M
Grubbs, RH
[J]. TETRAHEDRON LETTERS, 1999, 40 (08) : 1425 - 1428
[7] An efficient synthesis of valienamine via ring-closing metathesis
Chang, YK
Lee, BY
Kim, DJ
Lee, GS
Jeon, HB
Kim, KS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08): : 3299 - 3302
[8] Enantioselective ring expansion of prolinols and ring-closing metathesis:: formal synthesis of (-)-swainsonine
DeChamps, Ingrid
Pardo, Domingo Gomez
Cossy, Janine
[J]. ARKIVOC, 2007, : 38 - 45
[9] Ring-closing metathesis in an enantioselective synthesis of the macrocyclic core of crassin acetate
Herstad, Gunnar
Molesworth, Peter P.
Miller, Charlotte M.
Benneche, Tore
Tius, Marcus A.
[J]. TETRAHEDRON, 2016, 72 (17) : 2084 - 2093
[10] Synthesis of coumarins by ring-closing metathesis
Chatterjee, AK
Toste, FD
Goldberg, SD
Grubbs, RH
[J]. PURE AND APPLIED CHEMISTRY, 2003, 75 (04) : 421 - 425

← 1 2 3 4 5 →