A double iodoetherification of σ-symmetric diene acetals for installing four stereogenic centers in a single operation: Short asymmetric total synthesis of rubrenolide

Angewandte Chemie - International Edition

Volumn 44, Issue 5, 2005, Pages 734-737

  Fujioka, Hiromichi ^a   Ohba, Yusuke ^a   Hirose, Hideki ^a   Murai, Kenichi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Domino reactions; Natural products; Synthetic methods

Indexed keywords

MOLECULES; SYNTHESIS (CHEMICAL);

CHIRALS; ETHERIFICATION; RUBRENOLIDE; TETRAHYDROFURAN;

ACETAL RESINS;

ACETAL DERIVATIVE; NATURAL PRODUCT; RUBRENOLIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; ETHERIFICATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

ACETALS; ALKENES; ETHERS; IODINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; SPECTROPHOTOMETRY, INFRARED;

EID: 13444250054     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461584     Document Type: Article

References (24)

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9. Diallyl aldehyde 4 a (R = H) and phenyl aldehyde 4b (R = Ph) are known compounds (for 4a, see; B. B. Snider, B. R. Smith, Tetrahedron 2002, 58, 25-34; for 4b, see: W. A. Nugent, J. Feldman, J. C. Calabrese, J. Am. Chem. Soc. 1995, 117, 8992-8998). Diallylmethyl aldehyde (4c, R = Me) was prepared from the known diallyl ester 15b (obtained by methylation of 15a; see above reference for 4a) first by reduction of the ester and then oxidation with pyridinium dichromate. (diagram presented)
10. In our previous work (Ref. [1], alcohols were used as nucleophiles, whereas here the use of water instead afforded the hydroxyaldehyde by intramolecular haloetherification followed by opening of the eight-membered hemiacetal ring (coll = 2,4,6-collidine, H. Fujioka, H. Kitagawa, Y. Kita, unpublished results). (diagram presented)
11. CCDC-244868 contains the supplementary crystallo-graphic data for this paper. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.
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23. 3 was also effective.
24. 3).