Asymmetric synthesis, structure, and reactivity of unexpectedly stable spiroepoxy-β-lactones including facile conversion to tetronic acids: Application to (+)-maculalactone A

Journal of Organic Chemistry

Volumn 74, Issue 13, 2009, Pages 4772-4781

  Duffy, Richard J ^a,b   Morris, Kay A ^a   Vallakati, Ravikrishna ^a   Zhang, Wei ^a,c   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b Bldg 142   (United States)

^c ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; ALKYLIDENE; ANOMERIC EFFECT; ANTIFOULING AGENTS; ASYMMETRIC SYNTHESIS; CHEMICAL EQUATIONS; ENANTIOSELECTIVE SYNTHESIS; FACILE CONVERSION; HETEROCYCLES; NATURAL PRODUCTS; OPTICALLY ACTIVE; REACTIVITY PATTERN; SPIROHETEROCYCLES; SYNTHETIC UTILITY; TETRONIC;

ACIDS; CHEMICAL REACTIVITY; CHLORINE COMPOUNDS; OLIGOMERS; SYNTHESIS (CHEMICAL);

X RAY CRYSTALLOGRAPHY;

2,6 DIBENZYL (1,4 DIOXASPIRO[2.3] HEXAN 5 ONE; AMIDE; ANTIFOULING AGENT; CHLORIDE; DIETHYLAMINE; HATERUMALIDE TETRAHYDROFURAN; HETEROCYCLIC COMPOUND; HYDROCINNAMOYL CHLORIDE; KETENE DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; MACULALACTONE A; NUCLEOPHILE; PROPIOLACTONE; SPIRO COMPOUND; TETRAHYDROFURAN DERIVATIVE; TETRONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; BIOFILM; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; DIMERIZATION; ELIMINATION REACTION; ENANTIOSELECTIVITY; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

BENZOFURANS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; EPOXY COMPOUNDS; FURANS; LACTONES; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 67649610395     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900499e     Document Type: Article

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