Two Total Syntheses of Trigoxyphins K and L.

Autor: Li S; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom., O'Hanlon JA; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom., Mattimoe A; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom., Pickford HD; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom., Harwood LA; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom., Wong LL; Department of Chemistry, University of Oxford, Inorganic Chemistry Laboratory, South Parks Road, Oxford OX1 3QR, United Kingdom.; Oxford Suzhou Centre for Advanced Research, Ruo Shui Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, People's Republic of China., Robertson J; Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom.; Oxford Suzhou Centre for Advanced Research, Ruo Shui Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, People's Republic of China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Oct 20; Vol. 25 (41), pp. 7507-7511. Date of Electronic Publication: 2023 Oct 06.
DOI: 10.1021/acs.orglett.3c02796
Abstrakt: Two total syntheses are presented for trigoxyphins K and L, tricyclic terpenoids from Trigonostemon xyphophylloides . The first proceeds via electrophlic cyclization in A/C-ring substrates to close the B ring at C4-C5 and then 1 O 2 -mediated hydroxybutenolide formation to trigoxyphin L, with Luche reduction leading to trigoxyphin K. The second route develops from tetralone ring expansion to a B/C-ring intermediate that, by one-step O-demethylation-lactonization-isomerization, affords trigoxyphin K and then trigoxyphin L following enolate oxygenation.
Databáze: MEDLINE