270149 VO Strategies and Tactics in Organic Synthesis (2025S)

As its name suggests, this lecture aims at discussing how a complex molecule can be approached from a synthetic point of view. In order to do so, selected syntheses will be analysed and commented on. Emphasis shall be placed on retrosynthetic disconnections and their reduction to practice, on maximisation of synthetic efficiency and on the discussion of new methods in Organic Chemistry. Students will be encouraged to think creatively and suggest “out-of-the-box” approaches whenever possible.

For illustrative purposes, an Outline of the main broad topics to be covered and a pool of possible case-studies (typically 1 per lecture) are presented below.

OUTLINE and CASE-STUDY POOL

Sample case-studies

1. Classical approaches to complex molecules

a) Woodward, Strychnine

b) Woodward, Reserpine

c) Corey, Prostaglandins

d) Still, Periplanone B

e) Curran, Hirsutene and Capnellene

f) Corey, Gingkolide

2. Biomimetic approaches

a) Nicolaou, Endiandric Acids

b) Heathcock, Daphnyphillium alkaloids

c) Johnson, Steroids

d) Pirrung, Isocomene

e) Nicolaou, Bisorbicillinoids

f) Shair, Longithorone A

g) Sorensen, FR 182877

3. The past and the future

a) Overman, Strychnine (vs. 1a)

b) Stork, Quinine (vs. Woodward)

c) Volhardt, Steroids (vs. 2c)

d) Grubbs, Capnellene (vs. 1e)

e) Winkler, Manzamine A

f) Corey, Onocerin

g) Baran, Hapalindoles

h) Gin, Batzelladine A

(sample syntheses listed are only illustrative and not all of them will be covered!)