Hetero Diels-Alder reaction of olefin with o-quinone methides generated using (±)-binolphosphoric acid for the stereoselective synthesis of 2,4-diarylbenzopyrans: application to the formal synthesis of myristinin B/C

被引：44

作者：

Gharpure, Santosh J. ^{[1
,2
]}

Sathiyanarayanan, A. M. ^{[1
]}

Vuram, Prasanna K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

[2] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

RSC ADVANCES | 2013年 / 3卷 / 40期

关键词：

VINYLOGOUS CARBONATES; HYDROXYBENZYL ALCOHOLS; BIOMIMETIC SYNTHESIS; IN-SITU; CYCLIZATION; ALKYLATION; QUINONEMETHIDES; CONSTRUCTION; INHIBITORS; PHENOLS;

D O I：

10.1039/c3ra43526a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hetero Diels-Alder reaction of olefin with o-quinone methides (o-QMs) generated using (+/-)-binolphosphoric acid was developed for the stereoselective synthesis of 2,4-diarylbenzopyrans. The method thus developed was utilized in the formal synthesis of myristinin B/C.

引用

页码：18279 / 18282

页数：4

共 8 条

[1] Synthesis of α- and β-Lapachone Derivatives from Hetero Diels-Alder Trapping of Alkyl and Aryl o-Quinone Methides
da Silva, Fernando de C.
Ferreira, Sabrina B.
Kaiser, Carlos R.
Pinto, Angelo C.
Ferreira, Vitor F.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2009, 20 (08) : 1478 - 1482
[2] Recent advances in the application of Diels-Alder reactions involving o-quinodimethanes, aza-o-quinone methides and o-quinone methides in natural product total synthesis
Yang, Baochao
Gao, Shuanhu
CHEMICAL SOCIETY REVIEWS, 2018, 47 (21) : 7926 - 7953
[3] ORGN 388-Synthesis of 1,4-benzodioxane based Neolignans using o-quinone hetero-Diels-Alder reaction
Zhang, Jinsong
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
[4] Asymmetric synthesis of R-Mimosifoliol using a novel asymmetric inverse demand Diels-Alder reaction of an O-quinone methide with a chiral enol ether.
Selenski, C
Pettus, TRR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U332 - U332
[5] One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels-Alder reaction of o-quinone methide with unactivated dienes
Liu, Jian
Wang, Xiaoxiao
Xu, Lubin
Hao, Zhihui
Wang, Liang
Xiao, Jian
TETRAHEDRON, 2016, 72 (47) : 7642 - 7649
[6] Formal synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) via a highly double-stereoselective hetero Diels-Alder reaction directed by a (Salen)CoII catalyst and chiral diene
Hu, YJ
Huang, XD
Yao, ZJ
Wu, YL
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08): : 2456 - 2461
[7] Asymmetric hetero Diels-Alder reaction of N-benzylimines derived from R-glyceraldehyde: A new approach to homochiral piperidine building blocks and its application to the synthesis of (2R)-4-oxopipecolic acid
Badorrey, R
Cativiela, C
DiazdeVillegas, MD
Galvez, JA
TETRAHEDRON LETTERS, 1997, 38 (14) : 2547 - 2550
[8] DIELS-ALDER REACTION OF 4,6-DIHYDROTHIENO[3,4-C]FURAN-5,5-DIOXIDE WITH QUINONES - STEREOSELECTIVE SYNTHESIS OF QUINONE-ANNELATED 2,3-BIS(METHYLENE)-7-OXABICYCLO[2.2.1]HEPTANES
SUZUKI, T
KUBOMURA, K
TAKAYAMA, H
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (08) : 2164 - 2166

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