Total Syntheses of the Gregatins A-D and Aspertetronin A: Structure Revisions of These Compounds and of Aspertetronin B, Together with Plausible Structure Revisions of Gregatin E, Cyclogregatin, Graminin A, the Penicilliols A and B, and the Huaspenones A

Heike Burghart-Stoll; Reinhard Brückner

doi:10.1002/ejoc.201200207

Total Syntheses of the Gregatins A-D and Aspertetronin A: Structure Revisions of These Compounds and of Aspertetronin B, Together with Plausible Structure Revisions of Gregatin E, Cyclogregatin, Graminin A, the Penicilliols A and B, and the Huaspenones A

European Journal of Organic Chemistry ◽

10.1002/ejoc.201200207 ◽

2012 ◽

Vol 2012 (21) ◽

pp. 3978-4017 ◽

Cited By ~ 21

Author(s):

Heike Burghart-Stoll ◽

Reinhard Brückner

Keyword(s):

Total Syntheses ◽

Plausible Structure

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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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