The 3‐Hydroxypiperidine Skeleton: Key Element in Natural Product Synthesis

Abstract

The 3‐hydroxypiperidine moiety is a privileged scaffold that is encountered in many bioactive compounds and natural products. This review summarizes the investigations ofvarious research groups concerning the synthesis of natural products containing this scaffold.

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

“…The majority of the reported syntheses [2–4 32–35] are elaborate (far more than 10 steps), specific on one of the targets depicted in Fig. 1 and therefore on one relative configuration (either cis - or trans ), and have not been proven to be scalable.…”

A Practical and Enantiospecific Synthesis of (−)‐(R)‐ and (+)‐(S)‐Piperidin‐3‐ols

“…In the majority of natural products, the so-called privileged skeletal fragments can be identified. One of the important classes of skeletal frameworks present in diverse array of biologically active natural and unnatural products are chiral piperidin-3-ols [1]. Benidipine (1) [2a], cisapride (2) [2b], and pseudoconhydrine (3) [3] are some of the important biologically active compounds which possess piperidin-3-ol moieties in their structures (Fig.…”

Azacycloalkanes from epoxides and aziridines

“…Compounds of these groups show the antitumor, antidiabetes, antibacterial, and antiviral action [47][48][49][50]. The advances in the chemistry of saturated fi ve-and six-membered azaheterocycles were described in recent reviews [51][52][53][54][55].…”