Total Synthesis of Hamigerans and Analogues Thereof. Photochemical Generation and Diels-Alder Trapping of Hydroxy-o-quinodimethanes

Journal of the American Chemical Society

Volumn 126, Issue 2, 2004, Pages 613-627

  Nicolaou, K C ^a   Gray, David L F ^a   Tae, Jinsung ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; OXIDATION; PHOTOCHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

NATURAL PRODUCTS;

AROMATIC COMPOUNDS;

1,2 DICARBONYL DERIVATIVE; BENZALDEHYDE; ESTER; HAMIGERAN A; HAMIGERAN B; HAMIGERAN DERIVATIVE; HAMIGERAN E; HYDROXY 2 QUINODIMETHANE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

ANIMALS; CYCLIZATION; NAPHTHOQUINONES; PHOTOCHEMISTRY; POLYCYCLIC COMPOUNDS; PORIFERA; QUINONES;

EID: 0347087231     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030498f     Document Type: Article

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52. The hamigeran diastereoisomeric pairs were modeled with Accelrys Insight II, 1998. Molecular dynamics calculations were performed with Accelrys Discover v. 2.98 on a cluster of SGI Origin servers running Irix 6.5. The relative energies of the diastereoisomeric were computed with the class II pairwise force field cff91 v. 2.0 (see: Dinur, U.; Hagler A. In Reviews in Computational Chemistry; Lipkowitz, K., Boyd, D., Eds.; VCH: New York, 1991; Vol. 2, p 527), with library parameters for bond, valence, torsion, and out-of-plane terms. A total of 1000 structures were generated within 300 ps at 800 K. They were annealed to 300 K in 5 ps. The structures were further minimized to convergence using a conjugate gradient algorithm, and the lowest energy structure cluster was selected as the preferred structure. We thank Dr. C. N. C. Boddy for performing these calculations.