Concepedia

Total Synthesis of (−)-Laurequinone

Hironobu Takahashi, Yasutoshi Tonoi, Keiji Matsumoto, Hiroyuki Minami, Yoshiyasu Fukuyama

Chemistry Letters · 1998 · 11 citations · 14 references

DOI

Concepts

Abstract

Abstract The first synthesis of (−)-laurequinone, cyclolaurane-type sesquiterpenoid isolated from the red alga Laurencia nidifica, has been achieved by using an intramolecular Heck reaction and an insertion of carbene as the key steps for the construction of quaternary carbon at the benzylic position and cyclopropane ring, respectively.

References

14

Laurinterol, debromolaurinterol and isolaurinterol, constituents of Laurencia intermedia Yamada

Toshi Irie, M. Suzuki, E. KUROSAWA et al. · Tetrahedron · 1970 · 116 citations

, , +4

A remarkable substituent effect on the enantioselectivity of tandem asymmetric epoxidation and enantiospecific ring expansion of cyclopropylidene alcohols: a new enantiocontrolled synthesis of (-)-debromoaplysin and (-)-aplysin

Hideo Nemoto, Masatoshi Nagamochi, Hiroki Ishibashi et al. · The Journal of Organic Chemistry · 1994 · 88 citations

, , +5

Total synthesis of (.+-.)-scopadulcic acid A. An illustration of the utility of palladium catalyzed polyene cyclizations

David J. Kucera, Stephen O’Connor, Larry E. Overman · The Journal of Organic Chemistry · 1993 · 78 citations

, , +5

Total synthesis of (R,R)-crinan via regiospecific and stereoselective palladium catalysed cyclisation.

Ronald Grigg, Vijayaratnam Santhakumar, Visuvanathar Sridharan et al. · Tetrahedron · 1993 · 65 citations

, , +7

Halogenated and Non-halogenated Aromatic Sesquiterpenes from the Red Algae <i>Laurencia okamurai</i> Yamada

Minoru Suzuki, Etsurô Kurosawa · Bulletin of the Chemical Society of Japan · 1979 · 54 citations · Full text

, , +15