Seco‐Casbanes from the Australian Rainforest: ECD Predictions Key for Determining Remote Absolute Configuration1. Issue 9 (8th March 2016)

• Record Type: Journal Article
• Authors: Maslovskaya, Lidia A.; Savchenko, Andrei I.; Gordon, Victoria A.; Reddell, Paul W.; Pierce, Carly J.; Parsons, Peter G.; Williams, Craig M.
• Is Part Of: European journal of organic chemistry. Issue 9(2016)
• Page Start: 1673
• Page End: 1677
• Publication Date: 2016-03-08
• Subjects: Natural products -- Terpenoids -- Antitumor agents; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501605
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The seco ‐casbane framework, first isolated from Croton insularis, is surprisingly rare. Further evaluation of this Australian rainforest plant unearthed two additional members, EBC‐328 and EBC‐363. TD DFT predicted electronic circular dichroism (ECD) spectra were critical for remote absolute stereochemical determination. EBC‐328 displayed cytotoxic activity towards leukemia cells (K562). Potential biosynthetic relationships are discussed. Abstract : seco ‐Casbanes, which are considered very rare natural products, have only recently joined the ranks of other rarely occurring seco diterpenes, such as seco ‐lathyranes and seco ‐phorboids. Described herein are two further examples, EBC‐328 and EBC‐363 isolated from Croton insularis . TD DFT predicted ECD spectra were crucial for solving remote absolute stereochemistry.