1006606-91-2Relevant academic research and scientific papers
Total synthesis and structure-activity investigation of the marine natural product neopeltolide
Custar, Daniel W.,Zabawa, Thomas P.,Hines, John,Crews, Craig M.,Scheidt, Karl A.
supporting information; experimental part, p. 12406 - 12414 (2010/01/29)
The total synthesis and biological evaluation of neopeltolide and analogs are reported. The key bond-forming step utilizes a Lewis acid-catalyzed intramolecular macrocyclization that installs the tetrahydropyran ring and macrocycle simultaneously. Independent of each other, neither the macrolide nor the oxazole side chain substituents of neopeltolide can inhibit the growth of cancer cell lines. The biological data of the analogs indicate that alterations to either the ester side chain or the stereochemistry of the macrolide result in a loss of biological activity.
Total synthesis and structural revision of the marine macrolide neopeltolide
Custar, Daniel W.,Zabawa, Thomas P.,Scheidt, Karl A.
, p. 804 - 805 (2008/09/20)
The total synthesis and structural revision of the marine natural product neopeltolide is reported. The key bond-forming step involves a Lewis acid-catalyzed intramolecular cyclization to install the tetrahydropyran ring and the macrocycle simultaneously. This type of cyclization is the first of its kind and assembles the carbon backbone of the natural product efficiently. The synthesis of the reported structure revealed differences in the data between the natural and synthetic material. After significant investigation, the diastereomeric molecule with the C11 and C13 configurations inverted was synthesized using the initial route. This compound matches the data reported for neopeltolide (1H, 13C, HRMS, IR, NOESY, [α]), thereby establishing the correct overall structure for this potent macrolide natural product, including the relative and absolute stereochemistry. Copyright
