LV 270095-VO

Strategies and Tactics in Organic Synthesis

Block-Lecture (in English)

LECTURE STARTS MONDAY MARCH 19 at 10h00 @HS4!

DateTimePlace
Mo19 Mar10h to 12hHS-4

1. Übungsblatt: Revisiting Reserpine.

Di20 Mar10h to 12hHS-3
Di10 Apr10h to 12hHS-3

2. Übungsblatt: More Reserpine and Pericyclic Rxns.

Mi11 Apr10h to 12hHS-4
Fr13 Apr09h to 11hHS-3
Di17 Apr10h to 12hHS-3 Lecture cancelled!
Mi18 Apr10h to 12hHS-4
Di24 Apr10h to 12hHS-4
Mi25 Apr10h to 12hHS-4

3. Übungsblatt: Radical domino reactions.

Di8 May10h to 12hHS-4
Mi9 May10h to 12hHS-4
Di15 May10h to 12hHS-4

4. Übungsblatt: Metathesis.

Mi16 May10h to 12hHS-4
Exam6 June10h to 12hHS-4

Additional exam dates:

July 31, 15h00 to 17h00

September 6, 15h00 to 17h00

As its name suggests, this lecture aims at discussing how complex organic compounds 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 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!)

 

Literature:

Classics in Total Synthesis I, Nicolaou et al
Classics in Total Synthesis II, Nicolaou et al
The Logic of Chemical Synthesis, Corey