878-47-7Relevant articles and documents
Biocatalytic Approaches to the Enantiomers of Wieland–Miescher Ketone and its Derivatives
Bertuletti, Susanna,Bayout, Ikram,Bassanini, Ivan,Ferrandi, Erica E.,Bouzemi, Nassima,Monti, Daniela,Riva, Sergio
, p. 3992 - 3998 (2021/04/09)
Biocatalytic approaches have been investigated in order to isolate the enantiomers of Wieland–Miescher ketone (1) and of its alcoholic derivatives (cis-2 and trans-3). Specifically, two enzymes from our in-house metagenomic collection of oxidoreductases, IS2-SDR and Dm7α-HSDH, catalyzed the kinetic resolution of the starting racemic ketone 1 or its complete conversion into two diastereomeric products, respectively. Moreover, the kinetic resolution of the racemic cis-alcohol (2) was very efficiently obtained (E?2.000) by lipase PS catalyzed acetylation in dry acetone. All the products were isolated with ee≥95 %. Simple chemical elaborations of some of them allowed to isolate the missing enantiomers.
Total synthesis of JBIR-03 and asporyzin C
Murokawa, Tetsuro,Enomoto, Masaru,Teranishi, Takaaki,Ogura, Yusuke,Kuwahara, Shigefumi
, p. 4107 - 4109 (2018/10/15)
The first enantioselective total synthesis of JBIR-03 and asporyzin C, indole diterpenoids of fungal origin exhibiting a range of pharmacologically important biological activities, has been accomplished from a known bicyclic keto alcohol in 13 and 14 steps, respectively. A hydroxy-directed cyclopropanation and Pd(II)-mediated indole ring formation were exploited as the key steps to obtain a pivotal pentacylic intermediate, which was converted into asporyzin C via chain elongation using cross-metathesis and then into JBIR-03 by Pd(II)-catalyzed tetrahydrofuran ring formation in an exclusively diastereoselective manner.
Viridin analogs derived from steroidal building blocks
Viswanathan, Kishore,Ononye, Sophia N.,Cooper, Harold D.,Kyle Hadden, M.,Anderson, Amy C.,Wright, Dennis L.
, p. 6919 - 6922,4 (2020/09/02)
Naturally occurring furanosteroids such as viridin and wortmannin have long been known as potent inhibitors of the lipid kinase PI-3K. We have been interested in directly accessing analogs of these complex natural products from abundant steroid feedstock materials. In this communication, we describe the synthesis of viridin/wortmannin hybrid molecules from readily available building blocks that function as PI-3K inhibitors and maintain their electrophilic properties. The compounds also show anti-proliferative effects against a breast cancer line.
