Synthetic studies toward bioactive cyclic peroxides from the marine sponge Plakortis angulospiculatus.
[reaction: see text] The total synthesis of two stereoisomers of a bioactive cyclic peroxide isolated from the marine sponge Plakortis angulospiculatus has been achieved in 18 steps with an overall yield of 2.8%. Diels-Alder addition of singlet oxygen to an acyclic triene carboxylic acid precursor was used to construct the 3,6-dihydro-1,2-dioxin ring. By comparing spectral data of the synthesized compounds and the natural material, we tentatively assign the absolute stereochemistry for the natural product as 3S,6R,8S,10R.
Yao
Gang
G
Department of Chemistry, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Steliou
Kosta
K
D000447:Aldehydes; D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D010545:Peroxides