Abstract
AbstractPermethyl ether 1 from Tolypothrix conglutinata was synthesized following the retrosynthetic analysis of Scheme 1. According to it, we combined aldehyde 3 [prepared from S‐glycidol (7); cf. Schemes 2, 3] and lactone 4 (also prepared from S‐glycidol (7); cf. the preceding communication[2] and Scheme 4) to the enantiopure and diastereopure trimethoxy lactone 2 (Scheme 5). The CO group of this lactone was removed through the Criegee rearrangement of a derived lactol peroxonosylate (Scheme 6); thereby, the CCO bond of lactone 2 was replaced with complete retention of configuration by one COH bond of the resulting syn‐configured diol 18. Protecting group manipulations (Schemes 6, 7) and oxidation of the resulting alcohol 21 to aldehyde 31 (Scheme 10) initiated the three final operations: C2‐homologation with Ph3PCH‐CHO (→ enal 32), tosyl hydrazone formation (→ 34), and reduction/concomitant CC bond migration. They led to the target ether 1 as a 89:11 mixture with the CHCH‐richer ether 36.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.