A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid

2019 ◽  
Vol 21 (23) ◽  
pp. 9729-9733 ◽  
Author(s):  
Adam A. H. Elmehriki ◽  
James L. Gleason
Keyword(s):  
Total Synthesis ◽  
Puraquinonic Acid ◽  
Quaternary Carbons

scholarly journals Contiguous Quaternary Carbons: A Selection of Total Syntheses

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3841
Author(s):  
Alina Eggert ◽  
Christoph Etling ◽  
Dennis Lübken ◽  
Marius Saxarra ◽  
Markus Kalesse
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Status Quo ◽  
Total Syntheses ◽  
The Status ◽  
Selection Of ◽  
Quaternary Carbons

Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons.

Total Synthesis of Buergerinin F via Effective Construction of the Asymmetric Quaternary Carbons Using an Enantioselective Aldol Reaction.

ChemInform ◽  
2005 ◽  
Vol 36 (51) ◽  
Author(s):  
Isamu Shiina ◽  
Yo-ichi Kawakita ◽  
Ryoutarou Ibuka ◽  
Kazutoshi Yokoyama ◽  
Yu-suke Yamai
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Quaternary Carbons

Total synthesis of the complex taxane diterpene canataxpropellane

Science ◽  
2020 ◽  
Vol 367 (6478) ◽  
pp. 676-681 ◽  
Author(s):  
Fabian Schneider ◽  
Konstantin Samarin ◽  
Simone Zanella ◽  
Tanja Gaich
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent ◽  
Alder Reaction ◽  
Diels Alder ◽  
Core Structure ◽  
Natural Sources ◽  
The Core ◽  
Diels Alder Reaction ◽  
Cyclobutane Ring ◽  
Quaternary Carbons

Canataxpropellane belongs to the medicinally important taxane diterpene family. The most prominent congener, Taxol, is one of the most commonly used anticancer agent in clinics today. Canataxpropellane exhibits a taxane skeleton with three additional transannular C–C bonds, resulting in a total of six contiguous quaternary carbons, of which four are located on a cyclobutane ring. Unfortunately, isolation of canataxpropellane from natural sources is inefficient. Here, we report a total synthesis of (–)-canataxpropellane in 26 steps and 0.5% overall yield from a known intermediate corresponding to 29 steps from commercial material. The core structure of the (–)-canataxpropellane (2) was assembled in two steps using a Diels–Alder/ortho-alkene-arene photocycloaddition sequence. Enantioselectivity was introduced by designing chiral siloxanes to serve as auxiliaries in the Diels–Alder reaction.

A Concise Total Synthesis of (R)-Puraquinonic Acid

2013 ◽  
Vol 125 (12) ◽  
pp. 3526-3529 ◽  
Author(s):  
Erica A. Tiong ◽  
Daniel Rivalti ◽  
Benjamin M. Williams ◽  
James L. Gleason
Keyword(s):  
Total Synthesis ◽  
Puraquinonic Acid
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