259656-95-6Relevant academic research and scientific papers
A Non-Aldol Preparation of Enantiopure Propionate-Derived Motifs with the Assistance of Chiral Sulfoxides: Application to a Convergent Synthesis of the Lactone Core of Octalactins
Bauder, Claude
, p. 5402 - 5413 (2015/08/24)
Propionate-derived fragments were prepared by a non-aldol method using chiral sulfoxide chemistry. A methacrylate ester, assisted by a chiral sulfoxide as an auxiliary agent, was easily transformed into an optically pure allylic alcohol, which was then su
An Evans-Tishchenko-ring-closing metathesis approach to medium-ring lactones
Aird, Jennifer I.,Hulme, Alison N.,White, John W.
, p. 631 - 634 (2007/10/03)
A new approach to the synthesis of medium-ring lactones is reported based on sequential Evans-Tishchenko and ring-closing metathesis (RCM) reactions. High diastereoselectivity (>95:5) is demonstrated in the Evans-Tishchenko reaction of unsaturated aldehyd
Total synthesis of octalactin A via ring-closing metathesis reaction
Buszek, Keith R,Sato, Nagaaki,Jeong, Youngmee
, p. 181 - 184 (2007/10/03)
A new total synthesis of the novel lactone natural product octalactin A is described. The key step involves the facile construction of the eight-membered lactone core via ring-closing metathesis (RCM). This oxocene was elaborated to give the powerful anti
Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A.
Drouet,Ling,Tran,Theodorakis
, p. 207 - 210 (2007/10/03)
[structure: see text] Reveromycin A (1) belongs to a family of microbial polyketides with unusual structural features and biological activities. The structure of 1 is composed of a [6,6] spiroketal core decorated with highly unsaturated side chains. As a
Stereoselective total synthesis of reveromycin B and C19-epi-reveromycin B
Drouet, Keith E.,Theodorakis, Emmanuel A.
, p. 1987 - 2001 (2007/10/03)
Our studies toward the total synthesis of the reveromycin family of natural products are described herein. Our synthetic approach is efficient, stereocontrolled, and convergent and has resulted in the first synthesis of reveromycin B (4) and C19-epi-reveromycin B (55). Key steps of this successful strategy include: a modified Negishi coupling (construction of C7-C8 bond) and a Kishi-Nozaki reaction (construction of C19-C20 bond), which were employed in the attachment of the target side chains. The key building blocks for the total synthesis were thus defined as vinyl iodide 6, alkyne 7, and alkyne 8. Our synthesis illustrates the utility of the modified Negishi coupling for the construction of complex dienes, confirms the proposed stereochemistry of reveromycins and paves the way for the preparation of designed analogues for biological study.
