Total synthesis of epi-otteliones

Organic Letters

Volumn 4, Issue 17, 2002, Pages 2881-2884

  Mehta, Goverdhan ^a   Islam, Kabirul ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOHEXANONE DERIVATIVE; ETHER DERIVATIVE; OTTELIONE A; OTTELIONE B; TUBERCULOSTATIC AGENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROCHARITACEAE; MEDICINAL PLANT; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; ANTITUBERCULAR AGENTS; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANONES; ETHERS; HYDROCHARITACEAE; MOLECULAR STRUCTURE; PLANTS, MEDICINAL;

EID: 0041819306     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026263a     Document Type: Article

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16. 2), 121.10 (CH), 117.04 (CH)
17. o) and 0.2258 for all 5198 data. GOF = S = 0.917, restrained GOF = 0.917 for all data. An ORTEP drawing (excluding the hexane molecule for clarity) with 50% ellipsoidal probability is shown below. (figure presented) Fig. 3. ORTEP of p-nitrobenzoate derivative of 19.
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19. Ylide-mediated bisacetal opening in 14 leads to intermediate i in which bridgehead isomerization to ii takes place. Interestingly, the stereochemistry of the endo-aldehyde group remains secured during the Wittig reaction conditions. (figure presented)
20. Upon ozonolysis, 16 reverts back to 14 through intramolecular cascade acetalization, thus securing the cis-hydrindane stereochemistry and the integrity of the endo-vinyl group.
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