Novel Stereocontrolled Approach tosyn- andanti-Oxepene–Cyclogeranyltrans-Fused Polycyclic Systems: Asymmetric Total Synthesis of (−)-Aplysistatin, (+)-Palisadin A, (+)-Palisadin B, (+)-12-Hydroxy-Palisadin B, and the AB Ring System of Adociasulfate-2 and Toxicol A

Abstract An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter. Graphic Abstract

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Asymmetric Total Synthesis of Propindilactone G, Part 2: Enantioselective Construction of the Fully Functionalized BCDE Ring System

Chemistry - An Asian Journal ◽

10.1002/asia.201600130 ◽

2016 ◽

Vol 11 (9) ◽

pp. 1414-1424 ◽

Cited By ~ 12

Author(s):

Jia-Jun Zhang ◽

Lin You ◽

Yue-Fan Wang ◽

Yuan-He Li ◽

Xin-Ting Liang ◽

...

Keyword(s):

Total Synthesis ◽

Ring System ◽

Asymmetric Total Synthesis

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Studies Directed toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis)

The Journal of Organic Chemistry ◽

10.1021/jo00090a025 ◽

1994 ◽

Vol 59 (11) ◽

pp. 3055-3063 ◽

Cited By ~ 25

Author(s):

Pier F. Cirillo ◽

James S. Panek

Keyword(s):

Total Synthesis ◽

Ring System ◽

System A ◽

Ab Ring

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ChemInform Abstract: Studies Directed Toward the Synthesis of (+)-Sesbanimide A: Construction of the AB-Ring System (A Formal Total Synthesis).

ChemInform ◽

10.1002/chin.199451257 ◽

2010 ◽

Vol 25 (51) ◽

pp. no-no

Author(s):

P. F. CIRILLO ◽

J. S. PANEK

Keyword(s):

Total Synthesis ◽

Ring System ◽

System A ◽

Ab Ring

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Taxane Diterpene Synthesis Studies. Part 2: Towards Taxinine—Enantiospecific Construction of an AB-ring Substructure Incorporating both Quaternary Carbon Centres and Attempts to Annulate the C-ring

Australian Journal of Chemistry ◽

10.1071/ch03161 ◽

2004 ◽

Vol 57 (1) ◽

pp. 53 ◽

Cited By ~ 10

Author(s):

Martin G. Banwell ◽

Malcolm D. McLeod ◽

Andrew G. Riches

Keyword(s):

Total Synthesis ◽

Cycloaddition Reaction ◽

Ring System ◽

Diels Alder ◽

Biologically Active ◽

Allylic Oxidation ◽

Cope Rearrangement ◽

Rearrangement Reaction ◽

Ab Ring ◽

Active Natural

In connection with efforts to develop an efficient total synthesis of the biologically active natural product taxinine 1, the enzymatically-derived and monochiral cis-1,2-dihydrocatechol 7 was converted, over several steps including a Diels–Alder cycloaddition reaction, into the bicyclo[2.2.2]octan-2-one 18. Reaction of the last compound with the organocerium reagent 22 afforded the 1,5-diene 23 which engaged in an anionic oxy-Cope rearrangement reaction to give, after C-methylation of the product enolate 25, bicyclo[5.3.1]undecenone 27 embodying the AB-ring system of target 1. Two methods for allylic oxidation of such products were developed and several unsuccessful attempts to effect a cyclization reaction so as to establish the taxane C-ring are described.

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