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Synthesis and biological analysis of truncated calyculone H.


ABSTRACT: Herein, we report for the first time the design and linear synthesis of a truncated calyculone H (7) that lacks the telltale isopropyl/isopropylene groups, whereas the 12-membered macrocycle remains intact. Key steps for the framework of target molecule include allylic oxidation using SeO2, Sharpless asymmetric epoxidation, Barbier zinc allylation, and ring-closing metathesis (RCM) reactions. A second truncated "calyculone-like" analogue, 27, with a different oxidation pattern around the ring was also synthesized following a similar strategy. Screening for in vitro cytotoxicity against a panel of 60 human cancer cell lines revealed that 7 was as potent if not more so (for a few cell lines) than the natural product calyculone A (2).

SUBMITTER: Balasubramanyam P 

PROVIDER: S-EPMC5608098 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Synthesis and biological analysis of truncated calyculone H.

Balasubramanyam Penagaluri P   Rodríguez Abimael D AD  

Tetrahedron 20170114 9


Herein, we report for the first time the design and linear synthesis of a truncated calyculone H (<b>7</b>) that lacks the telltale isopropyl/isopropylene groups, whereas the 12-membered macrocycle remains intact. Key steps for the framework of target molecule include allylic oxidation using SeO<sub>2</sub>, Sharpless asymmetric epoxidation, Barbier zinc allylation, and ring-closing metathesis (RCM) reactions. A second truncated "calyculone-like" analogue, <b>27</b>, with a different oxidation p  ...[more]

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