Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine

Shen H. Tan; Martin G. Banwell; Anthony C. Willis; Tristan A. Reekie

doi:10.1021/ol3026846

Application of a Raney-Cobalt-Mediated Tandem Reductive Cyclization Protocol to Total Syntheses of the Aspidosperma Alkaloids (±)-Limaspermidine and (±)-1-Acetylaspidoalbidine

Organic Letters ◽

10.1021/ol3026846 ◽

2012 ◽

Vol 14 (22) ◽

pp. 5621-5623 ◽

Cited By ~ 44

Author(s):

Shen H. Tan ◽

Martin G. Banwell ◽

Anthony C. Willis ◽

Tristan A. Reekie

Keyword(s):

Reductive Cyclization ◽

Total Syntheses ◽

Raney Cobalt

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Total Syntheses of the 3H-Pyrrolo[2,3-c]quinolone-Containing Alkaloids Marinoquinolines A–F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

The Journal of Organic Chemistry ◽

10.1021/acs.joc.9b02725 ◽

2019 ◽

Vol 85 (2) ◽

pp. 650-663 ◽

Cited By ~ 3

Author(s):

Benoit Bolte ◽

Christopher S. Bryan ◽

Phillip P. Sharp ◽

Soheil Sayyahi ◽

Charly Rihouey ◽

...

Keyword(s):

Cross Coupling ◽

Reductive Cyclization ◽

Total Syntheses ◽

Palladium Catalyzed

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Total syntheses ofd-allo-1-deoxynojirimycin andl-talo-1-deoxynojirimycin via reductive cyclization

RSC Advances ◽

10.1039/c4ra06884j ◽

2014 ◽

Vol 4 (77) ◽

pp. 40852-40858 ◽

Cited By ~ 2

Author(s):

Subhash P. Chavan ◽

Nilesh B. Dumare ◽

Kailash P. Pawar

Keyword(s):

Reductive Cyclization ◽

Total Syntheses

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A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-b]indole Framework of the Uleine and Strychnos Alkaloids

The Journal of Organic Chemistry ◽

10.1021/jo302132d ◽

2012 ◽

Vol 77 (23) ◽

pp. 10773-10781 ◽

Cited By ~ 22

Author(s):

Tristan A. Reekie ◽

Martin G. Banwell ◽

Anthony C. Willis

Keyword(s):

Reductive Cyclization ◽

Raney Cobalt

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A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

The Journal of Organic Chemistry ◽

10.1021/acs.joc.6b01400 ◽

2016 ◽

Vol 81 (17) ◽

pp. 8022-8028 ◽

Cited By ~ 3

Author(s):

Shen H. Tan ◽

Martin G. Banwell ◽

Anthony C. Willis

Keyword(s):

Total Synthesis ◽

Reductive Cyclization ◽

Raney Cobalt

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A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine Alkaloid Gilbertine

The Journal of Organic Chemistry ◽

10.1021/acs.joc.6b01424 ◽

2016 ◽

Vol 81 (21) ◽

pp. 10551-10557 ◽

Cited By ~ 7

Author(s):

Fei Tang ◽

Martin G. Banwell ◽

Anthony C. Willis

Keyword(s):

Reductive Cyclization ◽

Raney Cobalt

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Ene-Reductase Permits Asymmetric Reductive Cyclization via Photoenzymatic Generation of Radicals

Synfacts ◽

10.1055/s-0040-1719570 ◽

2020 ◽

Vol 16 (12) ◽

pp. 1469

Keyword(s):

Reductive Cyclization

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Faculty Opinions recommendation of Mechanistic insights into polycycle formation by reductive cyclization in ikarugamycin biosynthesis.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.718339921.793494922 ◽

2014 ◽

Author(s):

Gong-Li Tang

Keyword(s):

Reductive Cyclization

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Development of Recent Total Syntheses Based on the Heck Reaction

Current Organic Chemistry ◽

10.2174/13852728113179990032 ◽

2013 ◽

Vol 17 (19) ◽

pp. 2192-2224 ◽

Cited By ~ 48

Author(s):

Majid Heravi ◽

Elaheh Hashemi ◽

Nazanin Ghobadi

Keyword(s):

Heck Reaction ◽

Total Syntheses

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Applications of Barton-McCombie Reaction in Total Syntheses

Current Organic Synthesis ◽

10.2174/157017941106141023113539 ◽

2014 ◽

Vol 11 (6) ◽

pp. 787-823 ◽

Cited By ~ 18

Author(s):

Majid Heravi ◽

Atefe Bakhtiari ◽

Zeinab Faghihi

Keyword(s):

Total Syntheses

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Formal Total Syntheses of Crocacin A-D

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20051696 ◽

2005 ◽

Vol 70 (10) ◽

pp. 1696-1708 ◽

Cited By ~ 12

Author(s):

Magnus Besev ◽

Christof Brehm ◽

Alois Fürstner

Keyword(s):

Natural Products ◽

Aldol Reaction ◽

Cross Coupling ◽

Coupling Reactions ◽

Total Syntheses ◽

Cross Coupling Reactions ◽

Palladium Catalyzed ◽

The Common ◽

Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

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