Biomimetic Synthesis and Studies Toward Enantioselective Synthesis of Flindersial Alkaloids. Issue 1 (26th March 2013)

• Record Type: Journal Article
• Authors: Vallakati, Ravikrishna; Lundy, Brian J.; Jansone‐Popova, Santa; May, Jeremy A.
• Is Part Of: Chirality. Volume 27:Issue 1(2015)
• Page Start: 14
• Page End: 17
• Publication Date: 2013-03-26
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22134
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>A strategy allowing both stereocontrol and control over structural isomer formation has been defined for the antimalarial flindersial alkaloids. The recently reported flinderoles were demonstrated to be derived from the natural product borrerine. The structural isomers of flinderoles, the borreverines, were also produced in vitro along with the flinderoles through the <named-content id="d210e718" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">dimerization</named-content> of borrerine in acidic conditions. This result is thought to replicate the biosynthesis of these compounds. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine can each be synthesized in three steps from tryptamine. Furthermore, progress toward a concise <named-content id="d210e724" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective synthesis</named-content> of flinderoles A, B, and C is described. This work includes <named-content id="d210e727" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective conjugate addition</named-content> to an unprotected indole‐appended enone. <italic>Chirality 27:14–17, 2015</italic>. © 2013 Wiley Periodicals, Inc.</p> </abstract>