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Volumn 75, Issue 19, 2010, Pages 6489-6501

Synthesis of the sponge-derived plakortone series of bioactive compounds

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ASYMMETRIC DIHYDROXYLATION; BIOACTIVE COMPOUNDS; BUTYRAMIDE; DOUBLE BONDS; ENOLATES; HOMOALLYLIC ALCOHOL; LACTONIZATION; PRIMARY ALCOHOLS; PSEUDOEPHEDRINE; SECONDARY METABOLITES; SIDE CHAINS; STANDARD PROCEDURES; STEREO-SELECTIVE; STEREOSPECIFIC; STERICALLY CONGESTED; TOTAL SYNTHESIS;

EID: 77957139471     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101224w     Document Type: Article
Times cited : (29)

References (39)
  • 26
    • 77957167629 scopus 로고    scopus 로고
    • The racemic C8-14 side chain was constructed from ester 41, converted to its phosphorane, and coupled with the aldehyde acquired from trans -(3 S,4 S,6 R)- 36 to yield 7,8-dehydroplakortone D. Attempts at regioselective reduction of the 7,8-d'uble bond were not successful. This information is presented in the Supporting Information.
    • The racemic C8-14 side chain was constructed from ester 41, converted to its phosphorane, and coupled with the aldehyde acquired from trans -(3 S,4 S,6 R)- 36 to yield 7,8-dehydroplakortone D. Attempts at regioselective reduction of the 7,8-double bond were not successful. This information is presented in the Supporting Information.
  • 31
    • 77957171246 scopus 로고    scopus 로고
    • Copies of spectra of plakortone D and the derived C11,12 diols were kindly provided by Drs. Patil and Freyer of Glaxo-Smith-Kline.
    • Copies of spectra of plakortone D and the derived C11,12 diols were kindly provided by Drs. Patil and Freyer of Glaxo-Smith-Kline.
  • 32
    • 77957163644 scopus 로고    scopus 로고
    • (Laval University) has presented a synthesis of plakortone D (see abstract OE9, Word Chemistry Congress, Brisbane)
    • Pr. J. Boukouvalas (Laval University) has presented a synthesis of plakortone D (see abstract OE9, 38th IUPAC Congress Frontiers in Chemistry, Word Chemistry Congress 2001, Brisbane).
    • (2001) 38th IUPAC Congress Frontiers in Chemistry
    • Boukouvalas, Pr.J.1
  • 36
    • 77957156381 scopus 로고    scopus 로고
    • This assumes there was no stereochemical compromise, e.g., at the allylic ethyl bearing position during the mild hydrogenation, consistent with the formation of a single dihydro derivative.
    • This assumes there was no stereochemical compromise, e.g., at the allylic ethyl bearing position during the mild hydrogenation, consistent with the formation of a single dihydro derivative.
  • 37
    • 77957160886 scopus 로고    scopus 로고
    • Communication from Professor Fattorusso, January 2010: The small discrepancies in the absolute values can be explained by the fact that we have registered our optical rotation on a very small amount (about 1 mg) of a not absolutely pure substance
    • Communication from Professor Fattorusso, January 2010: The small discrepancies in the absolute values can be explained by the fact that we have registered our optical rotation on a very small amount (about 1 mg) of a not absolutely pure substance.
  • 38
    • 77957163262 scopus 로고    scopus 로고
    • Unfortunately, no optical rotation was reported for synthesized plakortone B, in ref 10.
    • Unfortunately, no optical rotation was reported for synthesized plakortone B, in ref 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.