Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2018 Dec 21;83(24):14843-14852.
doi: 10.1021/acs.joc.8b02802. Epub 2018 Dec 7.

Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species

Matthew L Condakes  1 , Luiz F T Novaes  1 , Thomas J Maimone  1
Affiliations

Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species

Matthew L Condakes et al. J Org Chem. .

Abstract

Since the elucidation of the structure of anisatin in the late 1960s, sesquiterpene lactones from various Illicium species of plants have captivated synthetic chemists worldwide, resulting in a large body of synthetic work. In particular, Illicium sesquiterpenes containing the seco-prezizaane carbon framework have seen immense interest in recent years owing to desirable structural and medicinal attributes. This synopsis will focus on recently developed synthetic strategies to access these compact, highly oxidized terpenoids.

PubMed Disclaimer

Figures

Figure 1.
Figure 1.
(A) The seco-prezizaane skeleton and chemical structures of many highly-oxidized Illicium sesquiterpenes possessing it. (B) Other major Illicium sesquiterpene scaffolds, with representative example members.
Scheme 1.
Scheme 1.
Theodorakis’s 2011 Total Synthesis of (–)-Jiadifenin (3)
Scheme 2.
Scheme 2.
Zhai’s 2012 Total Synthesis of (–)-Jiadifenin (3)
Scheme 3.
Scheme 3.
Y. Fukuyama’s 2015 Formal Synthesis of (±)-Jiadifenin (3)
Scheme 4.
Scheme 4.
Micalizio’s 2016 Total Synthesis of (–)-Jiadifenin (3) and Related Majucinoids
Scheme 5.
Scheme 5.
Theodorakis’s 2011 Total Synthesis of (–)-Jiadifenolide (4)
Scheme 6.
Scheme 6.
Sorensen’s 2014 Synthesis of (–)-Jiadifenolide (4).
Scheme 7.
Scheme 7.
Paterson’s 2014 Total Synthesis of (±)-Jiadifenolide (4)
Scheme 8.
Scheme 8.
Zhang’s 2015 Total Synthesis and Gademann’s 2016 Formal Synthesis of (–)-Jiadifenolide (4)
Scheme 9.
Scheme 9.
Shenvi’s 2015 Gram-Scale Total Synthesis of (–)-Jiadifenolide (4)
Scheme 10.
Scheme 10.
T. Fukuyama’s 2012 Total Synthesis of (–)-Anisatin
Scheme 11.
Scheme 11.
Maimone’s 2016 Synthesis of (+)–Pesudoanisatin (6) from (+)–Cedrol
Scheme 12.
Scheme 12.
Maimone’s 2017 Synthesis of (–)-Majucin (2) and Related Majucinoids
See this image and copyright information in PMC

References

    1. Lane JF; Koch WT; Leeds NS; Gorin G On the Toxin of Illicium Anisatum. I. The Isolation and Characterization of a Convulsant Principle: Anisatin. J. Am. Chem. Soc 1952, 74, 3211
    2. Yamada K; Takada S; Nakamura S; Hirata Y The structure of anisatin Tetrahedron Lett. 1965, 52, 4797.
    1. Yamada K; Takada S; Nakamura S; Hirata Y The structures of anisatin and neoanisatin: Toxic sesquiterpenes from Illicium Anisatum L. Tetrahedron 1968, 24, 199.
    1. Fukuyama Y; Huang J-M Chemistry and neurotrophic activity of seco-prezizaane- and anislactone-type sesquiterpenes from Illicium species in Studies in Natural Products Chemistry (Atta-ur-Rahman, Ed.) 2005, 32, 395.
    1. Lidner DL; Doherty JB; Shoham G; Woodward RB Intramolecular ene reaction of glyoxylate esters: an anisatin model study. Tetrahedron Lett. 1982, 23, 5111.
    1. Kende AS; Chen J Stereoselective total synthesis of (±)-8-deoxyanisatin J. Am. Chem. Soc 1985, 107, 7184.

Publication types