Synthetic approach to potential precursors of sclerophytin A

Tetrahedron

Volumn 59, Issue 15, 2003, Pages 2729-2736

  Jung, Michael E ^a   Pontillo, Joseph ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Olefination; Potential precursors; Sclerophytin A

Indexed keywords

2 METHYL 8 OXABICYCLO[3.2.1]OCTAN 3 ONE; 2 [3 (CHLOROACETYLOXY)PROPYL] 2 METHYL 3,9 DIOXABICYCLO[4.2.1]NONAN 4 ONE; 2 [3 (CHLOROACETYLOXY)PROPYL] 2 METHYL 8 OXABICYCLO[3.2.1]OCTAN 3 ONE; 2 [3 [(1,1 DIMETHYL)ETHYLDIMETHYLSILYL]OXYPROPYL] 2 METHYL 3,9 DIOXABICYCLO[4.2.1]NONAN 4 ONE; 2 [3 [(1,1 DIMETHYL)ETHYLDIMETHYLSILYL]OXYPROPYL] 2,4 DIMETHYL 3,9 DIOXABICYCLO[4.2.1]NON 4 ENE; 5 [3 (2 METHYL 2 PROPENYL)] 2 (1 METHYL 1 TRIMETHYLSILYLOXY 4 PENTENYL)TETRAHYDROFURAN; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKADIENE; ALKANONE; ANTINEOPLASTIC AGENT; DELTA METHYL 5 (2 OXOPROPYL) DELTA TRIMETHYLSILYLOXYTETRAHYDROFURAN 2 BUTANAL; DELTA METHYL 5 (2 OXOPROPYL) DELTA TRIMETHYLSILYLOXYTETRAHYDROFURAN 2 BUTANOL; DITERPENE; ETHER DERIVATIVE; FURAN; KETONE DERIVATIVE; LACTONE DERIVATIVE; SCLEROPHYTIN A; SCLEROPHYTIN A DERIVATIVE; TRICHLOROACETONE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL MODIFICATION; CIS ISOMER; CYCLIZATION; DRUG SYNTHESIS; HYDROBORATION; ISOMER; METHYLATION; OXIDATION; PINACOL REARRANGEMENT; PRIORITY JOURNAL;

EID: 0037424852     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00283-7     Document Type: Article

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53. The conformations shown in B and C are not exact since the five-membered ring tends to rotate slightly to avoid eclipsing interactions in the basic envelope conformation. The energy calculations for B were fairly easy since it is the more stable isomer and all calculations converge on its structure. The energy calculations for C were done by constraining the structure so that at least one of the two alkyl groups was held in a pseudoaxial position since if no constraints were applied, the molecule rotated so that the two large groups were both in pseudoequatorial positions. Thus the energy difference cited is not exact but rather an estimate.