Toward a Total Synthesis of the Novel Polyketide Natural Product Spiculoic Acid A

2005 ◽  
Vol 7 (25) ◽  
pp. 5569-5572 ◽  
Author(s):  
Goverdhan Mehta ◽  
Uday Kumar Kundu
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
The Novel

scholarly journals Synthetic Studies toward (−)-Cleistenolide: Highly Stereoselective Synthesis of New γ-Lactone Subunits

2021 ◽  
Author(s):  
Suélen Sartori ◽  
Izabel Miranda ◽  
Davi de Matos ◽  
Markus Kohlhoff ◽  
Marisa Diaz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Acid Catalysis ◽  
Stereoselective Synthesis ◽  
Lactone Ring ◽  
Unsaturated Ester ◽  
The Novel ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure ◽  
Selective Protection

This study describes the stereoselective synthesis of two new γ-lactones in 6 and 3 steps and 19 and 32% yield, respectively, directed toward the total synthesis of the natural product (−)-cleistenolide. The starting material was an enantiomerically pure diacetonide diol, derived from d-mannitol with the required stereocenters for (−)-cleistenolide synthesis. γ-Lactone syntheses were based on highly selective protection and deprotection of hydroxyls from d-mannitol. The formation of γ-lactone rings was the culmination of this approach, made possible by a Horner-Wadsworth-Emmons Z-olefination between diacetal aldehyde and ethyl 2-(bis(o-tolyloxy)phosphoryl)acetate to produce an unsaturated ester. The Z-isomer ester was highly favored in relation to the E-isomer (Z/E ratio of 94:6), allowing the formation of the γ-lactone ring under acid catalysis. This strategy precluded the use of chiral auxiliaries or catalysts for the control of stereocenters in the novel γ-lactones.

Total synthesis of the marine natural product (+)-discodermolide in multigram quantities

2007 ◽  
Vol 79 (4) ◽  
pp. 685-700 ◽  
Author(s):  
Stuart J. Mickel
Keyword(s):  
Chemical Synthesis ◽  
Total Synthesis ◽  
Natural Product ◽  
Clinical Evaluation ◽  
Chemotherapeutic Agents ◽  
Marine Natural Product ◽  
The Novel

The novel polyketide (+)-discodermolide was isolated in very small quantities from sponge extracts. This compound is one of several microtubule stabilizers showing promise as novel chemotherapeutic agents for the treatment of cancer. The clinical evaluation of this and similar compounds is hampered by lack of material, and at present, the only way to obtain the necessary quantities is total chemical synthesis.

scholarly journals Toward a Total Synthesis of the Novel Polyketide Natural Product Spiculoic Acid A.

ChemInform ◽  
2006 ◽  
Vol 37 (18) ◽  
Author(s):  
Goverdhan Mehta ◽  
Uday Kumar Kundu
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
The Novel

Total synthesis of the putative structure of the novel triquinane natural product isocapnellenone

2002 ◽  
Vol 43 (46) ◽  
pp. 8301-8305 ◽  
Author(s):  
Goverdhan Mehta ◽  
A.Sai Krishna Murthy ◽  
Jayant D. Umarye
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
The Novel

Total Synthesis of the Putative Structure of the Novel Triquinane Natural Product Isocapnellenone.

ChemInform ◽  
2003 ◽  
Vol 34 (7) ◽  
Author(s):  
Goverdhan Mehta ◽  
A. Sai Krishna Murthy ◽  
Jayant D. Umarye
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
The Novel

Progress Toward The Total Synthesis Of The Marine Natural Product Karlotoxin 5

Planta Medica ◽  
2013 ◽  
Vol 79 (10) ◽  
Author(s):  
M Albadry ◽  
Y Zou ◽  
Y Takahashi ◽  
A Waters ◽  
M Hossein ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Marine Natural Product
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