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Biomimetic synthesis of (-)-longithorone A and synthesis of the ryanodine core

Record Type:	Electronic resources : Monograph/item
Title/Author:	Biomimetic synthesis of (-)-longithorone A and synthesis of the ryanodine core
Author:	Morales, Carl Andres.
Description:	371 p.
Notes:	Adviser: Matthew D. Shair.
Notes:	Source: Dissertation Abstracts International, Volume: 65-05, Section: B, page: 2421.
Contained By:	Dissertation Abstracts International65-05B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3131938
ISBN:	0496791788

Biomimetic synthesis of (-)-longithorone A and synthesis of the ryanodine core
Morales, Carl Andres.

Biomimetic synthesis of (-)-longithorone A and synthesis of the ryanodine core [electronic resource] - 371 p.

Adviser: Matthew D. Shair.

Thesis (Ph.D.)--Harvard University, 2004.

An enantioselective and biomimetic synthesis of (-)-longithorone A (1) has been accomplished. The synthesis takes inspiration from a proposed biosynthesis and demonstrates that an intermolecular-transannular Diels-Alder sequence is viable for the construction of the carbon framework of 1. [12]-Paracyclophanes possessing 1,3-disubstituted-1,3-dienes were synthesized in the first examples of ene-yne metathesis macrocyclization. Experiments designed to elucidate the mechanism of the macrocyclization suggest the intermediacy of terminal 1,3-dienes from alkyne-ethylene cross metathesis. Secondary benzylic alcohols were synthesized in high yield by enantioselective vinylzinc additions to electron rich benzaldehydes. This synthesis represents a unique example of chirality transfer in complex molecule synthesis; stereogenic centers are employed to control planar chirality, and planar chirality is then used to control stereogenic centers in the natural product.

ISBN: 0496791788Subjects--Topical Terms:

193634
Chemistry, Organic.

Biomimetic synthesis of (-)-longithorone A and synthesis of the ryanodine core
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502 $a Thesis (Ph.D.)--Harvard University, 2004.
520 # $a An enantioselective and biomimetic synthesis of (-)-longithorone A (1) has been accomplished. The synthesis takes inspiration from a proposed biosynthesis and demonstrates that an intermolecular-transannular Diels-Alder sequence is viable for the construction of the carbon framework of 1. [12]-Paracyclophanes possessing 1,3-disubstituted-1,3-dienes were synthesized in the first examples of ene-yne metathesis macrocyclization. Experiments designed to elucidate the mechanism of the macrocyclization suggest the intermediacy of terminal 1,3-dienes from alkyne-ethylene cross metathesis. Secondary benzylic alcohols were synthesized in high yield by enantioselective vinylzinc additions to electron rich benzaldehydes. This synthesis represents a unique example of chirality transfer in complex molecule synthesis; stereogenic centers are employed to control planar chirality, and planar chirality is then used to control stereogenic centers in the natural product.
520 # $a The racemic, unfunctionalized core of the natural product ryanodine ( 180) has been synthesized. The synthesis exploits a sequential double aldol strategy to construct the congested A-B-E ring system of 180 and uses the veiled symmetry in the natural product. Birch reduction and double alkylation were used to set two all carbon quaternary centers early in the synthetic route. The construction of the core represents a different route toward the natural product than that previously advanced and lays the foundation for a future completion of the synthesis of 218.
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