Cuparane, Laurane, Trichothecane

Xakagi, and S. Morii, Bull. Chem. Soc. Japan, 1976, 49, 3351. 

Reagents i, LiNPr a-DME ii, Mel iii, Br(CH2)40THP-HMPA iv p-TsOH-MeOH v, Ca-NHj-THF-HMPA vi, CrOj-HjO -MeaCO vii, CHjNj viii, NaNiSiMcjlj-DME ix, HCI,0°C x, DBU-xylene, A xi, silica gel-15% AgN03 xii, CH2=PPli3-DMSO xiii, MeOH-H xiv, HCI gas-CH2Cl2 xv, collidine. A xvi, LiAlH4 xvii, 10% NaOH xviii, Li-NH3-EtOH 

The ability of marine organisms to synthesize halogenated sesquiterpenoids cf. ref. 105 and pp. 66, 79, 101) is further illustrated by the isolation of the laurane-type compounds (77)-(79) from red seaweed (Laurencia glandulifera). The absolute configuration of aplysinol (80), a metabolite of various species of Lauren- 

McMillan and I. C. Paul, Tetrahedron Letters., 1976, 4219 the compound numbers in this paper are erroneous. 

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