Enantioselective Total Synthesis of the Antitumor Macrolide Rhizoxin D

The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)−C(9) fragment of the molecule was synthesized utilizing a threefold pseudosymmetric intermediate ultimately derived from γ-butyrolactone....

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Published inJournal of organic chemistry Vol. 68; no. 11; pp. 4215 - 4234
Main Authors Lafontaine, Jennifer A, Provencal, David P, Gardelli, Cristina, Leahy, James W
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.05.2003
Amer Chemical Soc
Subjects
Alkenes - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Indicators and Reagents
Lactones - chemical synthesis
Lactones - pharmacology
Macrolides
Molecular Structure
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Stereoisomerism
CARBON BOND FORMATION
1ST TOTAL SYNTHESIS
TRANSITION-METAL CATALYSIS
DESS-MARTIN PERIODINANE
ASYMMETRIC ALDOL REACTION
WADSWORTH-EMMONS REACTION
FUNGUS RHIZOPUS-CHINENSIS
MACROCYCLIC LACTONE ANTIBIOTICS
STEREOSELECTIVE SYNTHESES
CONTROLLED CARBOMETALATION
Enantioselectivity
Olefination
Alcohol
Lactone
Horner Emmons reaction
Oxygen heterocycle
Macrolide
Total synthesis
Cyclization
Polyenic compound
Lactonization
Chemical synthesis
Oxazole derivatives
Oxygen nitrogen heterocycle
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Abstract The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)−C(9) fragment of the molecule was synthesized utilizing a threefold pseudosymmetric intermediate ultimately derived from γ-butyrolactone. The central core of rhizoxin D was prepared via a chiral resolution/asymmetric aldol protocol. Several methods for the generation of the polyene fragment were explored, and the side-chain was ultimately prepared from serine in six steps. The unification of the left and right wings of the molecule was achieved using a one-step olefination protocol, and the macrocyclization was carried out using a Horner−Emmons olefination at the C(2)−C(3) olefin.
AbstractList The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)-C(9) fragment of the molecule was synthesized utilizing a threefold pseudosymmetric intermediate ultimately derived from gamma-butyrolactone. The central core of rhizoxin D was prepared via a chiral resolution/asymmetric aldol protocol. Several methods for the generation of the polyene fragment were explored, and the side-chain was ultimately prepared from serine in six steps. The unification of the left and right wings of the molecule was achieved using a one-step olefination protocol, and the macrocyclization was carried out using a Horner-Emmons olefination at the C(2)-C(3) olefin.
The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)−C(9) fragment of the molecule was synthesized utilizing a threefold pseudosymmetric intermediate ultimately derived from γ-butyrolactone. The central core of rhizoxin D was prepared via a chiral resolution/asymmetric aldol protocol. Several methods for the generation of the polyene fragment were explored, and the side-chain was ultimately prepared from serine in six steps. The unification of the left and right wings of the molecule was achieved using a one-step olefination protocol, and the macrocyclization was carried out using a Horner−Emmons olefination at the C(2)−C(3) olefin.
Author Gardelli, Cristina
Lafontaine, Jennifer A
Provencal, David P
Leahy, James W
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Issue 11
Keywords CARBON BOND FORMATION
1ST TOTAL SYNTHESIS
TRANSITION-METAL CATALYSIS
DESS-MARTIN PERIODINANE
ASYMMETRIC ALDOL REACTION
WADSWORTH-EMMONS REACTION
FUNGUS RHIZOPUS-CHINENSIS
MACROCYCLIC LACTONE ANTIBIOTICS
STEREOSELECTIVE SYNTHESES
CONTROLLED CARBOMETALATION
Enantioselectivity
Olefination
Alcohol
Lactone
Horner Emmons reaction
Oxygen heterocycle
Macrolide
Total synthesis
Cyclization
Polyenic compound
Lactonization
Chemical synthesis
Oxazole derivatives
Oxygen nitrogen heterocycle
Language English
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Snippet The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The...
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SubjectTerms Alkenes - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Indicators and Reagents
Lactones - chemical synthesis
Lactones - pharmacology
Macrolides
Molecular Structure
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Stereoisomerism
Title Enantioselective Total Synthesis of the Antitumor Macrolide Rhizoxin D
URI http://dx.doi.org/10.1021/jo034011x
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