Construction of the 5,10b-Phenanthridine Skeleton Using [3+2]-Cycloaddition of a Non-Stabilized Azomethine Ylide: Total Synthesis of (±)-Maritidine and (±)-Crinine Alkaloids

Ganesh Pandey; Nishant R. Gupta; Smita R. Gadre

doi:10.1002/ejoc.201001263

Construction of the 5,10b-Phenanthridine Skeleton Using [3+2]-Cycloaddition of a Non-Stabilized Azomethine Ylide: Total Synthesis of (±)-Maritidine and (±)-Crinine Alkaloids

European Journal of Organic Chemistry ◽

10.1002/ejoc.201001263 ◽

2010 ◽

Vol 2011 (4) ◽

pp. 740-750 ◽

Cited By ~ 27

Author(s):

Ganesh Pandey ◽

Nishant R. Gupta ◽

Smita R. Gadre

Keyword(s):

Total Synthesis ◽

Azomethine Ylide

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Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

Organic Letters ◽

10.1021/acs.orglett.1c00735 ◽

2021 ◽

Vol 23 (8) ◽

pp. 3058-3063

Author(s):

Seiya Katahara ◽

Yasukazu Sugiyama ◽

Mina Yamane ◽

Yukinori Komiya ◽

Takaaki Sato ◽

...

Keyword(s):

Total Synthesis ◽

Azomethine Ylide

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Synthetic Studies on Quinocarcin: Total Synthesis of (.+-.)-Quinocarcinamide via Dipole Cycloaddition of an Azomethine Ylide Generated by NBS Oxidation

The Journal of Organic Chemistry ◽

10.1021/jo00126a031 ◽

1995 ◽

Vol 60 (21) ◽

pp. 6791-6797 ◽

Cited By ~ 33

Author(s):

Mark E. Flanagan ◽

Robert M. Williams

Keyword(s):

Total Synthesis ◽

Azomethine Ylide ◽

Synthetic Studies

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Asymmetric, stereocontrolled total synthesis of (+) and (−)-spirotryprostatin B via a diastereoselective azomethine ylide [1,3]-dipolar cycloaddition reaction

Tetrahedron ◽

10.1016/s0040-4020(02)00630-0 ◽

2002 ◽

Vol 58 (32) ◽

pp. 6311-6322 ◽

Cited By ~ 63

Author(s):

Paul R Sebahar ◽

Hiroyuki Osada ◽

Takeo Usui ◽

Robert M Williams

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Azomethine Ylide ◽

Dipolar Cycloaddition

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ChemInform Abstract: Asymmetric, Stereocontrolled Total Synthesis of (+)- and (-)-Spirotryprostatin B via a Diastereoselective Azomethine Ylide [1,3]-Dipolar Cycloaddition Reaction.

ChemInform ◽

10.1002/chin.200250180 ◽

2010 ◽

Vol 33 (50) ◽

pp. no-no

Author(s):

Paul R. Sebahar ◽

Hiroyuki Osada ◽

Takeo Usui ◽

Robert M. Williams

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Azomethine Ylide ◽

Dipolar Cycloaddition

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ChemInform Abstract: Synthetic Studies on Quinocarcin: Total Synthesis of (.+-.)- Quinocarcinamide via Dipole Cycloaddition of an Azomethine Ylide Generated by NBS Oxidation.

ChemInform ◽

10.1002/chin.199610316 ◽

2010 ◽

Vol 27 (10) ◽

pp. no-no

Author(s):

M. E. FLANAGAN ◽

R. M. WILLIAMS

Keyword(s):

Total Synthesis ◽

Azomethine Ylide ◽

Synthetic Studies

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Total synthesis of tropinone using 1,3-dipolar cycloaddition of cyclic azomethine ylide and phenyl vinyl sulfone as the key step

Chemistry of Natural Compounds ◽

10.1007/s10600-010-9581-x ◽

2010 ◽

Vol 46 (2) ◽

pp. 254-256 ◽

Cited By ~ 10

Author(s):

Joydev K. Laha

Keyword(s):

Total Synthesis ◽

Azomethine Ylide ◽

Dipolar Cycloaddition ◽

Vinyl Sulfone ◽

Phenyl Vinyl

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Studies toward Total Synthesis of (±)-Caldaphnidine C via One-Pot Sequential Intramolecular Vilsmeier–Haack and Azomethine Ylide 1,3-Dipolar Cycloaddition

The Journal of Organic Chemistry ◽

10.1021/acs.joc.6b01835 ◽

2016 ◽

Vol 81 (19) ◽

pp. 9247-9268 ◽

Cited By ~ 13

Author(s):

Jonathan Boudreault ◽

François Lévesque ◽

Guillaume Bélanger

Keyword(s):

Total Synthesis ◽

Azomethine Ylide ◽

Dipolar Cycloaddition ◽

One Pot

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Stereospecific Route to 5,11-Methanomorphanthridine Alkaloids via Intramolecular 1,3-Dipolar Cycloaddition of Nonstabilized Azomethine Ylide: Formal Total Synthesis of (±)-Pancracine

Organic Letters ◽

10.1021/ol051321o ◽

2005 ◽

Vol 7 (17) ◽

pp. 3713-3716 ◽

Cited By ~ 39

Author(s):

Ganesh Pandey ◽

Prabal Banerjee ◽

Ravindra Kumar ◽

Vedavati G. Puranik

Keyword(s):

Total Synthesis ◽

Azomethine Ylide ◽

Dipolar Cycloaddition

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Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]-Cycloaddition of Platinum-Containing Azomethine Ylide

Chemistry - An Asian Journal ◽

10.1002/asia.201500491 ◽

2015 ◽

Vol 10 (9) ◽

pp. 1850-1853 ◽

Cited By ~ 13

Author(s):

Tomoya Ohyama ◽

Masako Uchida ◽

Hiroyuki Kusama ◽

Nobuharu Iwasawa

Keyword(s):

Total Synthesis ◽

Azomethine Ylide

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Stereoselective construction of 5,11-methanomorphanthridine and 5,10b-phenanthridine structural frameworks: Total syntheses of (±)-pancracine, (±)-brunsvigine, (±)-maritidine, and (±)-crinine

Pure and Applied Chemistry ◽

10.1351/pac-con-11-10-12 ◽

2012 ◽

Vol 84 (7) ◽

pp. 1597-1619 ◽

Cited By ~ 6

Author(s):

Ganesh Pandey ◽

Smita R. Gadre

Keyword(s):

Total Synthesis ◽

Core Structure ◽

Biologically Active ◽

Single Electron ◽

Azomethine Ylide ◽

Dipolar Cycloaddition ◽

Total Syntheses ◽

The Core ◽

One Step

The core structure of the complex pentacyclic 5,11-methanomorphanthridine skeleton and the vicinal quaternary and tertiary stereocenters of the 5,10b-phenanthridine skeleton are constructed stereospecifically in one step employing intramolecular 1,3-dipolar cycloaddition of a nonstabilized azomethine ylide (AMY) generated by the sequential double desilylation of appropriate bis-trimethylsilylmethyl amines using Ag(I)F as a single-electron oxidant. The strategy is successfully applied for the total synthesis of biologically active alkaloids such as (±)-pancracine, (±)-brunsvigine, (±)-maritidine, and (±)-crinine.

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