Glycal approach to the synthesis of macrolide (−)-A26771B

RSC Advances ◽  
2015 ◽  
Vol 5 (37) ◽  
pp. 29114-29120 ◽  
Author(s):  
Puli Saidhareddy ◽  
Arun K. Shaw
Keyword(s):  
Natural Product ◽  
Convergent Synthesis ◽  
Cross Metathesis ◽  
Yamaguchi Macrolactonization ◽  
Ferrier Rearrangement ◽  
Key Features

A convergent synthesis of macrolide natural product (−)-A26771B starting from d-glucal is reported. Key features of this synthesis involve Ferrier rearrangement, cross metathesis of chiral fragments 3 and 4 and Yamaguchi macrolactonization.

Synthesis of the Troponoid Natural Product Nezukone Via Sequential Rearrangement of Two Isomeric Precursors

1993 ◽  
Vol 46 (12) ◽  
pp. 1941 ◽  
Author(s):  
MG Banwell ◽  
CJ Cowden ◽  
GL Gravatt ◽  
CEF Rickard
Keyword(s):  
Crystal Structure ◽  
Natural Product ◽  
X Ray ◽  
Key Features

Nezukone (1) has been synthesized in seven steps from the readily available Δ3-trinorcarene (4). Key features of the sequence used include formation of the bicyclic isomer (2) of compound (1). Base-promoted isomerization of compound (2) followed by acidic workup then produced the isolable but highly unstable heptafulvenol (3), an extended enolic tautomer of nezukone (1). Under mildly basic conditions compound (3) rearranged to give the natural product (1). The X-ray crystal structure of the ring-fused cyclobutanone (8) is reported.

Convergent Synthesis and Discovery of a Natural Product-Inspired Paralog-Selective Hsp90 Inhibitor

2011 ◽  
Vol 13 (19) ◽  
pp. 5108-5111 ◽  
Author(s):  
Valer Jeso ◽  
Lisa Cherry ◽  
Todd K. Macklin ◽  
Subhas Chandra Pan ◽  
Philip V. LoGrasso ◽  
...  
Keyword(s):  
Natural Product ◽  
Hsp90 Inhibitor ◽  
Convergent Synthesis

Stereoselective Total Synthesis of Arundinolides A and B

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1576-1584
Author(s):  
Jun Liu ◽  
Zhi-Bing Dong ◽  
Caizhu Chang ◽  
Jialin Geng ◽  
Yinxin Liu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ethyl Lactate ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Key Features ◽  
First Time ◽  
Enantioselective Syntheses

The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-β-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction.

scholarly journals Catalytic Z-selective olefin cross-metathesis for natural product synthesis

Nature ◽  
2011 ◽  
Vol 471 (7339) ◽  
pp. 461-466 ◽  
Author(s):  
Simon J. Meek ◽  
Robert V. O’Brien ◽  
Josep Llaveria ◽  
Richard R. Schrock ◽  
Amir H. Hoveyda
Keyword(s):  
Natural Product ◽  
Natural Product Synthesis ◽  
Cross Metathesis
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