Evolution of the Total Synthesis of (−)-Okilactomycin Exploiting a Tandem Oxy-Cope Rearrangement/Oxidation, a Petasis−Ferrier Union/Rearrangement, and Ring-Closing Metathesis

An effective, asymmetric total synthesis of the antitumor antibiotic (−)-okilactomycin (1), as well as assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include a diastereoselective oxy-Cope rearrangement/oxidation sequence to i...

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Published inJournal of the American Chemical Society Vol. 131; no. 6; pp. 2348 - 2358
Main Authors Smith, Amos B, Bosanac, Todd, Basu, Kallol
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.02.2009
Amer Chemical Soc
Subjects
Acetals - chemistry
Aldehydes - chemical synthesis
Aldehydes - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
Lactones - chemical synthesis
Macrocyclic Compounds - chemical synthesis
Oxidation-Reduction
Physical Sciences
Pyrans - chemical synthesis
Pyrans - chemistry
Science & Technology
Stereoisomerism
Streptomyces - chemistry
OXIDATION
DIELS-ALDER
NATURAL-PRODUCTS
CARBONYL-COMPOUNDS
ORGANIC HALIDES
ALDEHYDES
CLAISEN REARRANGEMENT
SELENIUM DIOXIDE
DERIVATIVES
OKILACTOMYCIN
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Abstract An effective, asymmetric total synthesis of the antitumor antibiotic (−)-okilactomycin (1), as well as assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include a diastereoselective oxy-Cope rearrangement/oxidation sequence to install the C(1) and C(13) stereogenic centers, a Petasis−Ferrier union/rearrangement to construct the highly functionalized tetrahydropyranone inscribed within the 13-membered macrocycle ring, employing for the first time a sterically demanding acetal, an intramolecular chemoselective acylation to access an embedded bicyclic lactone, and an efficient ring-closing metathesis (RCM) reaction to generate the macrocyclic ring.
AbstractList An effective, asymmetric total synthesis of the antitumor antibiotic (-)-okilactomycin ( 1 ) and assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include: a diastereoselective oxy-Cope rearrangement/oxidation sequence to install the C(1) and C(13) stereogenic centers; a Petasis-Ferrier union/rearrangement to construct the highly functionalized tetrahydropyranone inscribed within the thirteen membered macrocycle ring, employing for the first time a sterically demanding acetal; an intramolecular chemoselective acylation to access an embedded bicyclic lactone; and an efficient ring closing metathesis (RCM) reaction to generate the macrocyclic ring.
An effective, asymmetric total synthesis of the antitumor antibiotic (-)-okilactomycin (1), as well as assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include a diastereoselective oxy-Cope rearrangement/oxidation sequence to install the C(1) and C(13) stereogenic centers, a Petasis-Ferrier union/rearrangement to construct the highly functionalized tetrahydropyranone inscribed within the 13-membered macrocycle ring, employing for the first time a sterically demanding acetal, an intramolecular chemoselective acylation to access an embedded bicyclic lactone, and an efficient ring-closing metathesis (RCM) reaction to generate the macrocyclic ring.
An effective, asymmetric total synthesis of the antitumor antibiotic (−)-okilactomycin (1), as well as assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include a diastereoselective oxy-Cope rearrangement/oxidation sequence to install the C(1) and C(13) stereogenic centers, a Petasis−Ferrier union/rearrangement to construct the highly functionalized tetrahydropyranone inscribed within the 13-membered macrocycle ring, employing for the first time a sterically demanding acetal, an intramolecular chemoselective acylation to access an embedded bicyclic lactone, and an efficient ring-closing metathesis (RCM) reaction to generate the macrocyclic ring.
Author Basu, Kallol
Bosanac, Todd
Smith, Amos B
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Keywords OXIDATION
DIELS-ALDER
NATURAL-PRODUCTS
CARBONYL-COMPOUNDS
ORGANIC HALIDES
ALDEHYDES
CLAISEN REARRANGEMENT
SELENIUM DIOXIDE
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Snippet An effective, asymmetric total synthesis of the antitumor antibiotic (−)-okilactomycin (1), as well as assignment of the absolute configuration, has been...
An effective, asymmetric total synthesis of the antitumor antibiotic (-)-okilactomycin (1), as well as assignment of the absolute configuration, has been...
An effective, asymmetric total synthesis of the antitumor antibiotic (-)-okilactomycin ( 1 ) and assignment of the absolute configuration, has been achieved...
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StartPage 2348
SubjectTerms Acetals - chemistry
Aldehydes - chemical synthesis
Aldehydes - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
Lactones - chemical synthesis
Macrocyclic Compounds - chemical synthesis
Oxidation-Reduction
Physical Sciences
Pyrans - chemical synthesis
Pyrans - chemistry
Science & Technology
Stereoisomerism
Streptomyces - chemistry
Title Evolution of the Total Synthesis of (−)-Okilactomycin Exploiting a Tandem Oxy-Cope Rearrangement/Oxidation, a Petasis−Ferrier Union/Rearrangement, and Ring-Closing Metathesis
URI http://dx.doi.org/10.1021/ja8084669
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https://www.ncbi.nlm.nih.gov/pubmed/19170499
https://search.proquest.com/docview/66914360
https://pubmed.ncbi.nlm.nih.gov/PMC2697663
Volume 131
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