Natural Product Synthesis

Selected Examples of Natural Products Synthesized by Our Group

Since time immemorial, our ancestors have been using a wide range of natural products to cure various diseases. However, several of these natural products are highly difficult to obtain and reproduce in the laboratory. Therefore, the research in natural product synthesis, both total and partial synthesis, is a significant field of investigation. Considered by many as a leading field in organic synthesis, natural product synthesis represents the power of chemical synthesis at any given time by attempting to push its frontiers into higher molecular complexity, diversity, and efficiency.

As an avenue for the application of our developed synthetic approaches, our laboratory is also highly interested in developing new drugs or exploring more efficient and step-economic routes to access biologically active compounds and natural products. To evaluate the potential of our synthesized compounds, we perform several tests to assess biological properties which include, but not limited to, anti-bacterial, anti-biofilm, antioxidant, and anticancer activity.

Selected works on natural product synthesis:

Concise Total Synthesis of Biologically Interesting Mallotophilippens C and E
(J. Org. Chem.200873 (11), pp 4313–4316)

Synthesis of Mallotophilippen-C 

Synthesis of Mallotophilippen-E

Mallotus philippinensis

Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: application to 3′-prenylrubranine and petiolin D regioisomer
(Tetrahedron 2011, 67, 9179)

3′-Prenylrubranine is commonly isolated from Mallotus philippinensis, distributed widely throughout Australia, tropical Asia including the Philippines. This plant exhibits potent antibacterial and antiallergic activities.

Total Synthesis of Chiricanine A, Arahypin-1, trans-Arachidin-2, trans-Arachidin-3, and Arahypin-5 from Peanut Seeds
(J. Nat. Prod. 2011, 74, 644)

Synthesis of trans-arachidin-2

Synthesis of trans-arachidin-3 and arahypin-5

Efficient and novel one-pot synthesis of polycycles bearing cyclols by FeCl3-promoted [2 + 2] cycloaddition: application to cannabicyclol, cannabicyclovarin, and ranhuadujuanine A
(Org. Biomol. Chem., 2014,12, 1250-1257)

Two-Step Synthetic Approach for the construction of carbazole alkaloids (Hyellazole & Chlorohyellazole)
(
Chem. Sci. 2015,  6, 7028)