Abstract
The bicyclo[4.3.0]nonane scaffold, commonly known as a hydrindane, is a common structural motif found in many terpenoid structures and one that remains a challenge for synthetic chemists to elaborate with appropriate regio- and stereo-selectivity. Over the course of the study of terpene natural products, the elaboration of the hydrindane structure has seen progress on the utilization of both old and newer methods to achieve the desired outcomes. This review seeks to serve as a general overview of these methods, and detail specific examples.
Highlights
Throughout the vast array of structures that polyterpenes and polyterpenoids can exist in, a common motif that appears regularly has been the bicyclo[4.3.0]nonane scaffold [1]
A sequential ring closing metathesis juncture. This methodology has been applied to the synthesis of norrisolide has been applied to the synthesis of norrisolide followed by Heck coupling was shown in 2010, giving a trans-hydrindane core for the C/D ring juncture [78]
We we have have presented presented methodology methodology that that has been been used used for for the the production production of of the the hydrindane hydrindane core.Here, The difficulty associated in the generation ofhas this scaffold lies not in the difficulty of the reactions core
Summary
Throughout the vast array of structures that polyterpenes and polyterpenoids can exist in, a common motif that appears regularly has been the bicyclo[4.3.0]nonane ( called hydrindane) scaffold [1]. Occurring terpenoids, functionalized terpene derivatives, are not just a structural curiosity, but play a central role in medicinal chemistry [1,3]. Their biological activity can range from anti-tumor activity to effects on cardiovascular systems (cardiac glycosides) to anti-inflammation [4,5,6,7,8,9]. Physaminimin acts an antibiotic and anti-inflammatory compound isolated from Physalis minima in southeastern China, and tested for nitric oxide synthase (NOS) activity in multiple cell lines [4].
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