First total synthesis of (-)-pericosine A from (-)-shikimic acid: Structure revision and determination of the absolute configuration of antitumor natural product pericosine A

Synlett

Volumn , Issue 10, 2006, Pages 1598-1600

  Usami, Yoshihide ^a   Horibe, Yusuke ^a   Takaoka, Isao ^a   Ichikawa, Hayato ^a   Arimoto, Masao ^a  

^a OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

Absolute configuration; Antitumor; Natural product; Pericosine A; Revised structure; Total synthesis

Indexed keywords

METHYL 6 CHLORO 3,4,5 TRIHYDROXY 1 CYCLOHEX 1 ENECARBOXYLATE; NATURAL PRODUCT; PERICOSINE A; SHIKIMIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 33745698028     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-944197     Document Type: Article

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14. 4 Similarly to our previous report, 12 was treated with dimethoxypropane and catalytic TsOH to afford a mixture of acetonides (17 as the major component and 18 as the minor component) as shown below, and its NOESY spectrum had cross peaks H-3/H-5, H-3, H-4/one of acetonide methyl groups in 17 and H-4′, H-5′/one of acetonide methyl groups in 18 (Scheme 2).
15. +: 223.0372; found: 223.0370.
16. D +104 (c, 0.04, EtOH).