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Volumn 45, Issue 51, 2004, Pages 9401-9403

Chiral synthesis of maconelliol: A novel cyclobutanoid terpene alcohol from pink hibiscus mealybug, Maconellicoccus hirsutus

Author keywords

Chiral synthesis; Cyclobutanoid terpene alcohol; Maconellicoccus hirsutus; Maconelliol; Sex pheromone

Indexed keywords

ALCOHOL DERIVATIVE; MACONELLIOL; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 8844220481     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.131     Document Type: Article
Times cited : (15)

References (16)
  • 6
    • 8844283462 scopus 로고    scopus 로고
    • note
    • Conversion of ketoacid 4 to hydroxyacid 5 without epimerization at both stereogenic centers was essential. We tried different conditions with purified (1R,3S) ketoacid 4 by crystallization (>96% ee) as precursor. Reaction of methylmagnesium chloride with (1R,3S) 4 formed an insoluble in THF intermediate bromomagnesium salt, the further reaction of which at the carbonyl group required either heating or sonication at rt. As a result, partial epimerization occurred at both centers. Methyllithium, on the other hand, gave with (1R,3S) 4 a THF-soluble carboxylate that reacted with an additional 1.2 equiv of MeLi at -20°C, but still ∼15% double epimerization took place. A solution has been found by reacting (1R,3S) 4 with 1.0 equiv MeLi at -20°C, followed by the addition of 1.6 equiv of MeMgCl, from which (1R,3S) 5 was isolated in 89% yield and 96% ee with virtually no change of chirality. This methodology will be used to scale up (R)-(-)-maconelliol 2 synthesis in the future
  • 9
    • 8844264627 scopus 로고    scopus 로고
    • note
    • 2 153.0916
  • 10
    • 8844254033 scopus 로고    scopus 로고
    • note
    • Chiral GC analysis was carried on a Hewlett Packard 6890 GC equipped with a 30 m × 0.25 mm ID, 0.25 μm film-thickness β-DEX 120 capillary column (Supeco, Inc., Bellefonte, PA) in the split mode (100:1) with hydrogen as carrier (55 cm/s, either 90 or 100°C isothermal)
  • 11
    • 8844237709 scopus 로고    scopus 로고
    • note
    • 2 168.1150
  • 15
    • 8844271807 scopus 로고    scopus 로고
    • note
    • 18O 154.1358


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.