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Volumn 44, Issue 7, 1996, Pages 1400-1403

Synthesis of (1α,7α,8β)-(±)-8-methyl-2-methylenebicyclo[5.3.0]dec- 5-en-8-ol. Structure revision of natural dictamnol

Author keywords

cyclization; dictamnol; Dictannus dasycarpus; pregeijerene; structure revision

Indexed keywords

NATURAL PRODUCT; PLANT EXTRACT; SESQUITERPENE;

EID: 0030036246     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1400     Document Type: Article
Times cited : (11)

References (20)
  • 2
    • 9344232274 scopus 로고    scopus 로고
    • note
    • The numbering system for azulenic compounds follows the numbering as given in structure I.
  • 8
    • 84989603736 scopus 로고
    • The small positive NOEs found in most small and medium-sized molecules are difficult to detect reliably by nuclear Overhauser and exchange spectroscopy (NOESY). partly because of sensitivity problems exacerbated by long relaxation delays needed between experiments: Morris G. A., Magn. Reson. Chem., 24, 371-403 (1986). Therefore, NOE difference spectroscopy instead of NOESY was used to determine NOEs in synthetic (±)-1 and natural dictamnol.
    • (1986) Magn. Reson. Chem. , vol.24 , pp. 371-403
    • Morris, G.A.1
  • 9
    • 9344248495 scopus 로고    scopus 로고
    • note
    • 1)
  • 18
    • 0343269944 scopus 로고
    • Preparative GC at 120 °C of the essential oil of the leaves of Amyris diatrypa SPRENGEL provided an almost pure sample of pregeijerene (7). At temperatures>120 °C Cope rearrangement to geijerene (9) took place. For example, see: Kubeczka K.-H., Phytochemistry, 13, 2017-2018 (1974).
    • (1974) Phytochemistry , vol.13 , pp. 2017-2018
    • Kubeczka, K.-H.1
  • 19
    • 9344228542 scopus 로고    scopus 로고
    • note
    • 13) it was assumed that air-induced cyclization of 7 also led to a racemic mixture, in this case (±)-dictamnol.
  • 20
    • 1542634032 scopus 로고
    • 12) 17) Sodium tert-amylate (2.2M in toluene) was prepared as described: Conia M. J.-M., Bull. Soc. Chim., 17, 537-541 (1950).
    • (1950) Bull. Soc. Chim. , vol.17 , pp. 537-541
    • Conia, M.J.-M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.