Literature DB >> 22081730

Total synthesis of (±)-γ-lycorane via the electrocyclic ring closure of a divinylpyrroline.

Raymond J Huntley1, Raymond L Funk.   

Abstract

A concise total synthesis of (±)-γ-lycorane is described. The key step in the synthesis is the 6π-electrocyclic ring closure of a divinylpyrroline to give a tetrahydroindole, which is subsequently hydrogenated to give the all-cis indolizidine core.

Entities:  

Year:  2011        PMID： 22081730      PMCID： PMC3212046          DOI： 10.1016/j.tetlet.2011.09.138

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

Review 1.  Amaryllidaceae and Sceletium alkaloids.

Authors:  J R Lewis
Journal:  Nat Prod Rep       Date:  1994-06       Impact factor: 13.423

2.  An approach to the total synthesis of welwistatin.

Authors:  Thomas J Greshock; Raymond L Funk
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

3.  Total syntheses of (+/-)-cis-trikentrin A and (+/-)-cis-trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines.

Authors:  Raymond J Huntley; Raymond L Funk
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

4.  Asymmetric nitroallylation of arylboronic acids with nitroallyl acetates catalyzed by chiral rhodium complexes and its application in a concise total synthesis of optically pure (+)-gamma-lycorane.

Authors:  Lin Dong; Yan-Jun Xu; Lin-Feng Cun; Xin Cui; Ai-Qiao Mi; Yao-Zhong Jiang; Liu-Zhu Gong
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

5.  Total synthesis of enantiopure (+)-gamma-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation.

Authors:  Bruno D Chapsal; Iwao Ojima
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

6.  Formal total synthesis of (+/-)-gamma-lycorane and (+/-)-1-deoxylycorine using the [4+2]-cycloaddition/rearrangement cascade of furanyl carbamates.

Authors:  A Padwa; M A Brodney; S M Lynch
Journal:  J Org Chem       Date:  2001-03-09       Impact factor: 4.354

7.  Electrocyclic ring-opening/pi-allyl cation cyclization reaction sequences involving gem-dihalocyclopropanes as substrates: application to syntheses of (+/-)-, (+)-, and (-)-gamma-lycorane.

Authors:  M G Banwell; J E Harvey; D C Hockless; A W Wu
Journal:  J Org Chem       Date:  2000-07-14       Impact factor: 4.354

8.  A general and efficient strategy for 7-aryloctahydroindole and cis-3a-aryloctahydroindole alkaloids: total syntheses of (+/-)-gamma-lycorane and (+/-)-crinane.

Authors:  Shuanhu Gao; Yong Qiang Tu; Zhenlei Song; Aixia Wang; Xiaohui Fan; Yijun Jiang
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

9.  Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.

Authors:  Thomas J Greshock; Raymond L Funk
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

10.  Intramolecular bromo-amination of 1,4-cyclohexadiene aminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (-)-gamma-lycorane.

Authors:  Hiromichi Fujioka; Kenichi Murai; Yusuke Ohba; Hideki Hirose; Yasuyuki Kita
Journal:  Chem Commun (Camb)       Date:  2005-11-29       Impact factor: 6.222
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  3 in total

1.  Facile Synthesis of 3-Amido-Dienynes via a Tandem α-Propargylation-Isomerization of Chiral Allenamides and their Applications in Diels-Alder Cycloadditions.

Authors:  Zhi-Xiong Ma; Li-Chao Fang; Richard P Hsung
Journal:  Synlett       Date:  2017-09-01       Impact factor: 2.454

Review 2.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036

Review 3.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411
  3 in total

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